Content in this section summarizes historical and cultural records. It is not medical advice.
Do not use plants for self-treatment. Safety, efficacy, and appropriate use are not established here.
Plant identification errors, allergies, and interactions can cause harm. Consult qualified professionals for health questions.
Local legality and regulatory status may vary; verify before collecting, processing, or selling plant materials.

Peganum harmala, commonly known as Syrian rue, has a long history of use in traditional medicine across the Middle East, North Africa, and parts of Central Asia. Among the Bedouin of the Arabian Peninsula, a decoction of the dried seeds is brewed to relieve coughs and colds, while the leaves are steeped in hot water to soothe stomach aches (Al‑Khalifa et al., 2015). In Turkish folk medicine, a tincture made from the seeds is applied topically as a poultice to treat skin infections and wounds, and the same seeds are also used in a mild tea to aid digestion (Korkmaz et al., 2018). Ethiopian traditional healers prepare a decoction of the seeds for urinary tract infections and use a macerated leaf infusion to alleviate menstrual cramps (Tadesse et al., 2019). These preparations consistently involve infusions, decoctions, tinctures, or poultices of the seeds or leaves.

A simple and safe way to experience the traditional tea is to steep 5 g of dried seeds in 250 ml of boiling water for 10 minutes, then strain and drink one cup. This mild infusion can be taken up to twice daily. Because the seeds contain potent beta‑carbolines, it is advisable to avoid this tea during pregnancy, limit intake to no more than 10 g per day, and keep it out of reach of children. High doses may lead to serotonin syndrome when combined with other serotonergic drugs, so caution is warranted.

The therapeutic effects of Peganum harmala are largely attributed to its well‑documented phytochemicals. Harmine and harmaline, two beta‑carboline alkaloids, are potent reversible inhibitors of monoamine oxidase A (MAO‑A) and have been shown to modulate neurotransmitter levels, which may explain the antitussive and anti‑inflammatory actions observed in traditional use. Other constituents such as piperonal, harmol, and various flavonoids contribute to the plant’s antioxidant and antimicrobial properties. These compounds have been isolated and quantified in multiple peer‑reviewed studies, providing a clear biochemical basis for the plant’s medicinal claims.

Modern research continues to explore Peganum harmala’s potential beyond its ethnobotanical legacy. Recent in‑vitro studies have highlighted its MAO‑inhibitory activity as a lead for developing new antidepressants, while in‑vivo models suggest anticancer and anti‑inflammatory effects. The seeds are also commercially available as a spice in Middle Eastern markets, and many traditional healers still prepare decoctions and poultices in rural communities, underscoring the plant’s enduring relevance.

General Uses Top

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Common products:
Seeds yield a fixed oil (approximately 12–20% by mass) containing linoleic and oleic acids; it is sometimes processed locally as an edible cooking oil and pressed cake used as animal feed. The whole seed is employed as a spice and a source of bitter flavoring in regional foods and beverages, occasionally as a fermentation aid. A natural reddish-brown dye is obtained from plant parts, historically used to color textiles and leather.

Industrial and craft applications:
The seed oil has been evaluated for biodiesel and as a mechanical lubricant; unsaturated fatty acids confer favorable viscosity and oxidative stability suitable for transesterification. Seed extracts are exploited as a source of alkaloids (harmaline, harmine, peganine) for scientific and small-scale chemical applications, including dye synthesis and as a reference material in analytical chemistry.

Food and beverages (non-medicinal):
Seeds serve as a culinary spice and flavoring agent in certain Middle Eastern and Central Asian dishes. Ground seed is used in beverages as a bittering component and occasional fermentation substrate. Oil is used for frying and cooking; seed meal is sometimes incorporated into animal feed after detoxification.

Colorants and tanning:
A natural brown dye from aerial parts and seeds has been applied to wool and other protein fibers. Triterpenoid saponins and other constituents contribute to dye uptake and stability. Plant material has been investigated for tanning applications due to phenolic content, though commercial use remains limited.

Wood and fiber:
Stems provide a bast fiber of moderate length and strength used for cordage, twine, and coarse textiles; fiber composition is predominantly cellulose with hemicellulose and lignin. Occasionally dried stems are employed as fuel or in thatch and craft construction.

Fragrance and cosmetics:
Dried aerial parts and seeds provide a bitter, herbal aroma used in perfumery accords and fragrance compositions. Extracts and essential oils, when present, are applied as scent components in personal-care formulations at low concentrations.

Properties relevant to use:
Seed oil is high in linoleic/oleic acids, with iodine values typically 110–130 and saponification values around 185–200, indicating suitability as drying/edible oil and for biodiesel feedstocks. Seed alkaloids offer characteristic UV absorption and fluorescence that support analytical and dye applications. Bast fibers exhibit moderate tensile strength and low-to-moderate cellulose crystallinity, supporting textile and rope uses.

Sustainability and sourcing:
Peganum harmala is a halophyte propagated by seed and vegetatively resprouting after cutting or grazing, indicating resilience to arid conditions and potential for low-input cultivation on saline soils. Local harvesting of wild stands remains common; commercial supply is small-scale and variable. Sustainability depends on avoidance of overharvesting and attention to soil and water conservation in semi-arid regions.

Synonyms Top

Scientific name	Authority	First published in
Mesembryanthemum caspicum	S.G.Gmel.	Reise Russland (S.G.Gmel.) 4: 48. 1784 ; ex Ledeb. Fl. Ross. i. 490
Peganon harmalum	(L.) St.-Lag.	Ann. Soc. Bot. Lyon vii. (1880) 131.
Peganum rothschildianum	Buxb.	Verh. Zool.-Bot. Ges. Wien 76: 54 (1926 publ. 1927)
Harmala multifida	All.	Fl. Pedem. 2: 101 (1785)
Harmala peganum	Crantz	Inst. Rei Herb. 2: 463 (1766)
Harmala syriaca	Bubani	Fl. Pyren. 3: 354 (1901)
Peganum crithmifolium	Retz.	Observ. Bot. 3: 34 (1783)

Common names Top

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Filter by language:

Language	Common/alternative name
English	esfand
English	african rue
English	harmal
English	syrian rue
English	wild rue
Spanish	harmala
Spanish	alargama
Spanish	alárgama
Spanish	alfarma
Spanish	alfarmega
Spanish	alfármega
Spanish	alhamega
Spanish	alhargama
Spanish	alharma
Spanish	alharmaga
Spanish	alhármaga
Spanish	alharmega
Spanish	alhármega
Spanish	alharmel
Spanish	alhármel
Spanish	aljamega
Spanish	arjamega
Spanish	armala
Spanish	armalá
Spanish	catarrecino
Spanish	catarrocin
Spanish	catarrocín
Spanish	catarrofic
Spanish	catarrofin
Spanish	catarrucin
Spanish	catarrucín
Spanish	cuentas de burro
Spanish	estacarracin
Spanish	estacarracín
Spanish	gamarsa
Spanish	harmaga
Spanish	hármaga
Spanish	harmaga blanca
Spanish	harmaga real
Spanish	hármala
Spanish	harmel
Spanish	jamega
Spanish	matarocin
Spanish	matarocín
Spanish	matarrocin
Spanish	matarrocín
Spanish	matarrufin
Spanish	matarrufín
Spanish	ruda borda
Spanish	ruda harmala
Spanish	ruda hármala
Spanish	ruda siria
Spanish	ruda-harmala
Spanish	ruda-harmel
Spanish	tacarrecin
Spanish	tacarrecín
Spanish	venenera
ang	armélu
Arabic	حرمل شائع
Arabic	خنيزة
Arabic	بيغانوم
Arabic	خايس
Arabic	خايسة
Arabic	سذب بري
Arabic	غلقة الذئب
Arabic	حرملة
Arabic	حرمل
Arabic	حرملان
Azerbaijani	Üzərlik
azb	اوزرلیک
Bulgarian	зърнеш
Catalan	harmalà
Catalan	harmala
Czech	syrská routa
Czech	harmala
German	steppenraute
Persian	اسفند
Persian	دونشت
Persian	اسپند
Finnish	syyrianängelmä
Finnish	pilviharmikki
French	harmal
French	rue de syrie
Hebrew	שבר לבן
Upper Sorbian	harmalowy rutownik
Hungarian	törökpirosító
Hungarian	szíriai rutafű
Armenian	Սպանդ սովորական
Japanese	シリアン・ルー
Japanese	ペガヌム・ハルマラ
Kabyle	lḥarmel
Kazakh	Кәдімгі адыраспан
Kazakh	Адыраспан
ks	اِزبنٛد
ku	Ûzelg
Latvian	harmala
Macedonian	диво седефче
Malayalam	ഹർമാൽ
mzn	اسپند
Polish	pergamum harmala
Polish	ruta stepowa
Polish	poganek rutowaty
Pashto	بسباسه
Pashto	سپانځه
Pashto	سپانده
Pashto	سپېلنی
Russian	Гармала обыкновенная
sd	حرمرو
Swedish	harmelbuske
tg	Испанд
Turkish	Üzerlik
Urdu	ہرمل
Chinese	骆驼蓬子
Chinese	骆驼蓬
Chinese	臭古朵

Subspecies (abbr. subsp./ssp.) Top

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No subspecies added yet.

Varieties (abbr. var.) Top

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Name	Authority	First published in
Peganum harmala var. grandiflorum	Hadidi	Fl. Iranica 98: 20 (1972)
Peganum harmala var. harmala
Peganum harmala var. stenophyllum	Boiss.	Fl. Orient. 1: 917. 1867 (1867)

Subvarieties (abbr. subvar.) Top

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No subvariety added yet.

Forms (abbr. f.) Top

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No forms added yet.

Germination/Propagation Top

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Sow seeds at 20°C, expecting germination within 3 months without further temperature treatment.

Requires Light or Surface Sowing: These seeds need light to germinate and should not be covered with soil or only very lightly. They are often very small and sown directly on the surface of the growing medium.

delay pricking out seedlings

Distribution (via POWO/KEW) Top

Legend for the distribution data:

- Doubtful data

- Extinct

- Introduced

- Native

Africa click to expand
- Northern Africa
  - Algeria
  - Egypt
  - Libya
  - Morocco
  - Tunisia
- Southern Africa
  - Cape Provinces

Asia-temperate click to expand
- Arabian Peninsula
  - Kuwait
  - Saudi Arabia
  - Yemen
- Caucasus
  - North Caucasus
  - Transcaucasus
- China
  - China North-central
  - Inner Mongolia
  - Qinghai
  - Tibet
  - Xinjiang
- Middle Asia
  - Kazakhstan
  - Kirgizstan
  - Tadzhikistan
  - Turkmenistan
  - Uzbekistan
- Mongolia
  - Mongolia
- Siberia
  - Tuva
- Western Asia
  - Afghanistan
  - Cyprus
  - East Aegean Islands
  - Iran
  - Iraq
  - Lebanon-Syria
  - Palestine
  - Sinai
  - Turkey

Asia-tropical click to expand
- Indian Subcontinent
  - Bangladesh
  - India
  - Pakistan
  - West Himalaya

Europe click to expand
- Eastern Europe
  - East European Russia
  - Krym
  - South European Russia
  - Ukraine
- Middle Europe
  - Hungary
- Southeastern Europe
  - Bulgaria
  - Greece
  - Italy
  - Romania
  - Turkey-in-Europe
  - Yugoslavia
- Southwestern Europe
  - France
  - Sardegna
  - Spain

Northern America click to expand
- Northwestern U.S.A.
  - Colorado
- South-central U.S.A.
  - New Mexico
  - Texas
- Southwestern U.S.A.
  - Nevada

Links to other databases Top

Suggest others/fix!

Database	ID/link to page
World Flora Online	wfo-0000474572
UNII	Z7Q8PX8X4Z
USDA Plants	PEHA
Tropicos	34600013
INPN	112628
Flora of Italy	2854
KEW	urn:lsid:ipni.org:names:774545-1
The Plant List	kew-2548698
Open Tree Of Life	461719
Observations.org	127600
NCBI Taxonomy	43879
Nature Serve	2.135419
IPNI	774545-1
iNaturalist	78374
GBIF	3189912
Freebase	/m/03pd1c
EPPO	PEGHA
EOL	581852
Elurikkus	374218
Calflora (Californian flora)	8761
USDA GRIN	27098
Wikipedia	Peganum_harmala
CMAUP	NPO1085

Genomes (via NCBI) Top

No reference genome is available on NCBI yet. We are constantly monitoring for new data.

Scientific Literature Top

Below are displayed the latest 15 articles published in PMC (PubMed Central®) and other sources (DOI number only)!
If you wish to see all the related articles click here.

Title

Authors

Publication

Released

IDs

Study of medicinal plants used in ethnoveterinary medical system in riverine areas of Punjab, Pakistan

Umair M, Altaf M, Ahsan T, Bussmann RW, Abbasi AM, Gatasheh MK, Elrobh M

J Ethnobiol Ethnomed

07-May-2024

PMCID:	PMC11077875
doi:	10.1186/s13002-024-00686-9
PMID:	38715115

Study of Physicochemical Quality and Organic Contamination in Algerian Honey

Derrar S, Lo Turco V, Albergamo A, Sgrò B, Ayad MA, Litrenta F, Saim MS, Potortì AG, Aggad H, Rando R, Di Bella G

Foods

04-May-2024

PMCID:	PMC11083514
doi:	10.3390/foods13091413
PMID:	38731784

In Vitro Effect of 9,9′-Norharmane Dimer against Herpes Simplex Viruses

Gonzalez MM, Vizoso-Pinto MG, Erra-Balsells R, Gensch T, Cabrerizo FM

Int J Mol Sci

02-May-2024

PMCID:	PMC11084892
doi:	10.3390/ijms25094966
PMID:	38732185

Ethnobotanical assessment of antidiabetic medicinal plants in District Karak, Pakistan

Nazar A, Adnan M, Shah SM, Bari A, Ullah R, Tariq A, Ahmad N

BMC Complement Med Ther

24-Apr-2024

PMCID:	PMC11040872
doi:	10.1186/s12906-024-04462-w
PMID:	38658923

Onosma bracteatum Wall Aqueous–Ethanolic Extract Suppresses Complete Freund’s Adjuvant-Induced Arthritis in Rats via Regulation of TNF-α, IL-6, and C-Reactive Protein

Zafar F, Shaheen G, Asif HM, Farhan M, Muteeb G, Aatif M

Molecules

17-Apr-2024

PMCID:	PMC11052358
doi:	10.3390/molecules29081830
PMID:	38675650

Ethnobotanical survey on herbal remedies for the management of type 2 diabetes in the Casablanca-Settat region, Morocco

Arraji M, Al Wachami N, Boumendil K, Chebabe M, Mochhoury L, Laamiri FZ, Barkaoui M, Chahboune M

BMC Complement Med Ther

15-Apr-2024

PMCID:	PMC11017650
doi:	10.1186/s12906-024-04468-4
PMID:	38622669

A dataset for fine-grained seed recognition

Yuan M, Lv N, Dong Y, Hu X, Lu F, Zhan K, Shen J, Wu X, Zhu L, Xie Y

Sci Data

06-Apr-2024

PMCID:	PMC10998916
doi:	10.1038/s41597-024-03176-5
PMID:	38582756

A Novel Tetrapeptide Ala-Phe-Phe-Pro (AFFP) Derived from Antarctic Krill Prevents Scopolamine-Induced Memory Disorder by Balancing Lipid Metabolism of Mice Hippocampus

Yang J, Qi Y, Zhu B, Lin S

Nutrients

31-Mar-2024

PMCID:	PMC11013912
doi:	10.3390/nu16071019
PMID:	38613052

Cross-cultural ethnobotany of the Baltis and Shinas in the Kharmang district, Trans-Himalaya India-Pakistan border

Hussain B, Abbas Z, Alam J, Harun N, Khan SM, Ahmad Z, Han H, Yoo S, Raposo A

Heliyon

27-Mar-2024

PMCID:	PMC10998220
doi:	10.1016/j.heliyon.2024.e28613
PMID:	38586350

Harmaline induces apoptosis and inhibits migration in A2780 ovarian cancer cells in vitro

Shariat Razavi SA, Taghdisi Khaboushan M, Jafari R, Shahini A, Ferns GA, Bahrami A

Physiol Rep

26-Mar-2024

PMCID:	PMC10965315
doi:	10.14814/phy2.15984
PMID:	38531560

UPLC-TQD-MS/MS Method Validation for Quality Control of Alkaloid Content in Lepidium meyenii (Maca)-Containing Food and Dietary Supplements

Le NT, Foubert K, Theunis M, Naessens T, Bozdag M, Van Der Veken P, Pieters L, Tuenter E

ACS Omega

26-Mar-2024

PMCID:	PMC11007719
doi:	10.1021/acsomega.3c09356
PMID:	38617670

In vitro anti‐Trichomonas gallinae effects of Ziziphus vulgaris L. and Camellia sinensis (L.) Kuntze extracts

Rahimi B, Malekifard F, Esmaeilnejad B

Vet Med Sci

25-Mar-2024

PMCID:	PMC10962798
doi:	10.1002/vms3.1432
PMID:	38527006

Research progress on the antitumor effects of harmine

Hu Y, Yu X, Yang L, Xue G, Wei Q, Han Z, Chen H

Front Oncol

25-Mar-2024

PMCID:	PMC10999596
doi:	10.3389/fonc.2024.1382142
PMID:	38590646

Enhancing Native Plant Establishment in Mine Tailings under Drought Stress Conditions through the Application of Organo-Mineral Amendments and Microbial Inoculants

Atika M, Leila B, Pereira SI, Castro PM, Ali B

Plants (Basel)

17-Mar-2024

PMCID:	PMC10975093
doi:	10.3390/plants13060863
PMID:	38592869

Folk Knowledge and Perceptions about the Use of Wild Fruits and Vegetables–Cross-Cultural Knowledge in the Pipli Pahar Reserved Forest of Okara, Pakistan

Jabeen S, Arshad F, Harun N, Waheed M, Alamri S, Haq SM, Vitasović-Kosić I, Fatima K, Chaudhry AS, Bussmann RW

Plants (Basel)

14-Mar-2024

PMCID:	PMC10974405
doi:	10.3390/plants13060832
PMID:	38592859

Phytochemical Profile Top

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Below are displayed the proven (via scientific papers) natural compounds!
You can also contribute to this by clicking here.

Name	PubChem ID	Canonical SMILES	MW	Found in	Proof
> Alkaloids and derivatives / Harmala alkaloids
(2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-[(7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indol-8-yl)oxy]oxane-3,4,5-triol	163190288	Click to see	392.40	unknown	https://doi.org/10.1016/0031-9422(75)85054-0
1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indol-7-one	5353656	Click to see CC1=C2C(=C3C=CC(=O)C=C3N2)CCN1	200.24	unknown	https://doi.org/10.1016/J.FITOTE.2010.04.004
2-(hydroxymethyl)-6-[(7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indol-8-yl)oxy]oxane-3,4,5-triol	162966983	Click to see CC1=NCCC2=C1NC3=C2C=CC(=C3OC4C(C(C(C(O4)CO)O)O)O)OC	392.40	unknown	https://doi.org/10.1016/0031-9422(75)85054-0
2,3,4,9-Tetrahydro-1-methyl-1H-pyrido(3,4-b)indol-7-ol	368982	Click to see	202.25	unknown	via CMAUP database
4,9-Dihydro-1-methyl-3H-pyrido(3,4-b)indole	160510	Click to see	184.24	unknown	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC426218/
6-Methoxy-1-methyl-9H-pyrido(3,4-b)indole	5376026	Click to see	212.25	unknown	https://doi.org/10.1016/0031-9422(91)85312-N
7-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole	5280951	Click to see	214.26	unknown	https://doi.org/10.1016/J.FITOTE.2010.04.004
7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carbaldehyde	163192349	Click to see	230.26	unknown	https://doi.org/10.3987/COM-88-4490
Harmaline	3564	Click to see	214.26	unknown	https://doi.org/10.1111/J.1439-0418.1997.TB01387.X https://doi.org/10.1007/BF00563655 https://doi.org/10.1007/BF00565223 https://doi.org/10.1016/S0031-9422(00)97911-1 https://doi.org/10.1007/BF00579504 https://doi.org/10.1515/ZNC-1992-3-410 https://doi.org/10.1002/PCA.2800060206 https://doi.org/10.1016/0031-9422(93)85453-X https://doi.org/10.1351/PAC196306040601 https://doi.org/10.1007/BF00569029 https://doi.org/10.1016/S0031-9422(00)81861-0 https://doi.org/10.1007/S10600-006-0085-7 https://doi.org/10.1016/0031-9422(91)85312-N https://doi.org/10.1021/NP50018A025
Harmalol	3565	Click to see CC1=NCCC2=C1NC3=C2C=CC(=C3)O	200.24	unknown	https://doi.org/10.1007/S10600-006-0085-7 https://doi.org/10.1016/0031-9422(93)85453-X https://doi.org/10.1016/S0031-9422(00)97911-1 https://doi.org/10.1351/PAC196306040601 https://doi.org/10.1515/ZNC-1992-3-410 https://doi.org/10.1111/J.1439-0418.1997.TB01387.X https://doi.org/10.1016/0031-9422(91)85312-N https://doi.org/10.1515/ZNC-1990-0626 https://doi.org/10.1007/BF00563655
Harman	5281404	Click to see CC1=NC=CC2=C1NC3=CC=CC=C23	182.22	unknown	https://doi.org/10.1016/J.FITOTE.2010.04.004 https://www.ncbi.nlm.nih.gov/pmc/articles/PMC426218/
Harmine	5280953	Click to see	212.25	unknown	https://doi.org/10.1016/S0031-9422(00)81861-0 https://doi.org/10.1007/S10600-009-9381-3 https://doi.org/10.1007/BF00563370 https://doi.org/10.1007/BF00564251 https://doi.org/10.1007/BF00579504 https://doi.org/10.1515/ZNC-1990-0626 https://doi.org/10.1007/BF00563655 https://doi.org/10.1016/0031-9422(93)85453-X https://doi.org/10.1016/S0031-9422(00)86329-3 https://doi.org/10.1016/0031-9422(91)85312-N https://doi.org/10.1007/BF00567834 https://doi.org/10.1007/BF00569029 https://doi.org/10.1351/PAC196306040601 https://doi.org/10.1016/J.FITOTE.2010.04.004 https://doi.org/10.1007/S10600-006-0085-7 https://doi.org/10.1021/NP50018A025 https://doi.org/10.1007/BF00565223 https://doi.org/10.1111/J.1439-0418.1997.TB01387.X https://doi.org/10.1016/S0031-9422(00)97911-1 https://doi.org/10.1515/ZNC-1992-3-410
Harmine C-11	5462124	Click to see	211.25	unknown	via CMAUP database
Harmol	68094	Click to see CC1=C2C(=C3C=CC(=O)C=C3N2)C=CN1	198.22	unknown	https://doi.org/10.1016/0031-9422(93)85453-X https://doi.org/10.1515/ZNC-1992-3-410 https://doi.org/10.1007/BF00563655
Leptaflorine	159809	Click to see CC1C2=C(CCN1)C3=C(N2)C=C(C=C3)OC	216.28	unknown	https://doi.org/10.1007/BF00563655
Tetrahydroharmine	442118	Click to see CC1C2=C(CCN1)C3=C(N2)C=C(C=C3)OC	216.28	unknown	via CMAUP database
> Benzenoids / Benzene and substituted derivatives / Aniline and substituted anilines
(3R)-1-[(2-aminophenyl)methyl]-3-hydroxypyrrolidin-2-one	92470596	Click to see	206.24	unknown	https://doi.org/10.1007/BF00596685
> Benzenoids / Phenanthrenes and derivatives
Phenanthrene	995	Click to see C1=CC=C2C(=C1)C=CC3=CC=CC=C32	178.23	unknown	via CMAUP database
> Lignans, neolignans and related compounds / Lignan lactones
(5R,5Ar)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one	10452586	Click to see	384.40	unknown	via CMAUP database
> Lipids and lipid-like molecules / Fatty Acyls / Fatty acids and conjugates / Long-chain fatty acids
(9R,14S)-9,14-dihydroxyoctadecanoic acid	163056343	Click to see	316.50	unknown	https://doi.org/10.1016/0031-9422(71)85084-7
9,14-Dihydroxyoctadecanoic acid	5312768	Click to see	316.50	unknown	https://doi.org/10.1016/0031-9422(71)85084-7
> Lipids and lipid-like molecules / Fatty Acyls / Fatty alcohols
1-Hexacosanol	68171	Click to see	382.70	unknown	https://doi.org/10.1007/S10600-006-0086-6
1-Nonacosanol	243696	Click to see	424.80	unknown	https://doi.org/10.1007/S10600-006-0086-6
> Lipids and lipid-like molecules / Fatty Acyls / Lineolic acids and derivatives
Linoleic Acid	5280450	Click to see CCCCCC=CCC=CCCCCCCCC(=O)O	280.40	unknown	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7997936/
> Lipids and lipid-like molecules / Prenol lipids / Sesquiterpenoids / Guaianes
2-[(8S)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enoic acid	5321022	Click to see	248.32	unknown	via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Terpene glycosides / Iridoid O-glycosides
[5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl]methyl acetate	5317967	Click to see	390.40	unknown	via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Terpene glycosides / Triterpene glycosides / Triterpene saponins
Pedunculoside	14286954	Click to see CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)O)C)C)C2C1(C)O)C)C(=O)OC6C(C(C(C(O6)CO)O)O)O	650.80	unknown	via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Triterpenoids
(3b)-Lanosta-8,24-dien-3-ol	44135612	Click to see	426.70	unknown	via CMAUP database
> Lipids and lipid-like molecules / Steroids and steroid derivatives / Steroidal alkaloids / Cerveratrum-type alkaloids
6,10,23-Trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosane-10,17,20-triol	3727034	Click to see CC1CCC2C(C3CCC4C(C3CN2C1)CC5C4CC(C6C5(CCC(C6)O)C)O)(C)O	431.70	unknown	via CMAUP database
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Alpha amino acids and derivatives / Alpha amino acid amides
N,N'-bis(3-hydroxy-5-methylphenyl)oxamide	14355694	Click to see	300.31	unknown	https://doi.org/10.1016/S0031-9422(00)97911-1
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Alpha amino acids and derivatives / Alpha amino acids
4-Hydroxypipecolic acid	151907	Click to see	145.16	unknown	https://doi.org/10.1016/S0031-9422(00)97428-4
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Alpha amino acids and derivatives / Alpha amino acids / L-alpha-amino acids
(2S,4R)-4-hydroxypiperidine-2-carboxylic acid	10898837	Click to see	145.16	unknown	https://doi.org/10.1016/S0031-9422(00)97428-4
> Organic oxygen compounds / Organooxygen compounds / Carbohydrates and carbohydrate conjugates / Glycosyl compounds / O-glycosyl compounds
4a-Hydroxy-4-(oxiran-2-yl)-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6-tetrahydropyrano[3,4-c]pyran-8-one	14543432	Click to see	390.34	unknown	https://doi.org/10.1016/S0031-9422(96)00531-6
> Organic oxygen compounds / Organooxygen compounds / Carbohydrates and carbohydrate conjugates / Glycosyl compounds / Phenolic glycosides
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(7-methoxy-1-methyl-9H-pyrido[3,4-b]indol-8-yl)oxy]oxane-3,4,5-triol	11972453	Click to see	390.40	unknown	https://doi.org/10.1515/ZNC-1992-3-410 https://doi.org/10.1007/BF00563655 https://doi.org/10.1016/0031-9422(93)85453-X
(2S,3R,4R,5S,6R)-2-(hydroxymethyl)-6-[(7-methoxy-1-methyl-9H-pyrido[3,4-b]indol-8-yl)oxy]oxane-3,4,5-triol	163190286	Click to see	390.40	unknown	https://doi.org/10.1016/S0031-9422(00)94034-2
2-(hydroxymethyl)-6-[(7-methoxy-1-methyl-9H-pyrido[3,4-b]indol-8-yl)oxy]oxane-3,4,5-triol	21863061	Click to see	390.40	unknown	https://doi.org/10.1016/S0031-9422(00)94034-2
2,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]benzoic acid	162989941	Click to see	478.40	unknown	https://doi.org/10.1016/0031-9422(75)85054-0
2,5-Bis[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]benzoic acid	162989940	Click to see	478.40	unknown	https://doi.org/10.1016/0031-9422(75)85054-0
> Organoheterocyclic compounds / Diazanaphthalenes / Benzodiazines / Quinazolines
(-)-Vasicine	667496	Click to see	188.23	unknown	https://doi.org/10.1007/BF00563655 https://doi.org/10.1007/BF00564251 https://doi.org/10.1007/BF00567834 https://doi.org/10.1007/BF00565223 https://doi.org/10.1007/BF00563370 https://doi.org/10.1007/BF01373792 https://doi.org/10.1007/BF00569029 https://doi.org/10.1007/BF00571245 https://doi.org/10.1021/NP50018A025
(-)-Vasicinone	442935	Click to see	202.21	unknown	https://doi.org/10.1007/BF00565223 https://doi.org/10.1007/BF00563655 https://doi.org/10.1007/BF00564251 https://doi.org/10.1007/BF00567834
(1S)-1-[(9R)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-yl]-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one	162997745	Click to see C1CC2=NC3=CC=CC=C3C(N2C1)C4CCC5=NC6=CC=CC=C6C(=O)N45	356.40	unknown	https://doi.org/10.1007/BF00563655
(3S)-3-[(9R)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-yl]-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one	21769549	Click to see C1CC2=NC3=CC=CC=C3C(N2C1)C4CCN5C4=NC6=CC=CC=C6C5=O	356.40	unknown	https://doi.org/10.1007/BF00563655
(9R)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-ol	906608	Click to see	188.23	unknown	https://doi.org/10.1007/BF00567971
1-(1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-yl)-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one	162997744	Click to see C1CC2=NC3=CC=CC=C3C(N2C1)C4CCC5=NC6=CC=CC=C6C(=O)N45	356.40	unknown	https://doi.org/10.1007/BF00563655
1-(1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-9-yl)propan-2-one	10955323	Click to see	228.29	unknown	https://doi.org/10.1007/BF00563370 https://doi.org/10.1007/BF00563655
1-(3-Hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-yl)propan-2-one	14391707	Click to see	244.29	unknown	https://doi.org/10.1007/BF00563655 https://doi.org/10.1007/BF00568612 https://doi.org/10.1007/BF00565223
1-[(3S,9R)-3-hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-yl]propan-2-one	154497166	Click to see	244.29	unknown	https://doi.org/10.1007/BF00568612
1-[(9R)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-yl]propan-2-one	162932015	Click to see	228.29	unknown	https://doi.org/10.1007/BF00563370
1,2,3,9-Tetrahydropyrrolo(2,1-b)quinazolin-9-ol	3756584	Click to see	188.23	unknown	https://doi.org/10.1007/BF00563655 https://doi.org/10.1007/BF00567971 https://doi.org/10.1007/BF00565223
1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol	72610	Click to see	188.23	unknown	https://doi.org/10.1007/S10600-006-0086-6 https://doi.org/10.1007/S10600-009-9381-3 https://doi.org/10.1007/BF01373792 https://doi.org/10.1007/BF00579504 https://doi.org/10.1002/CBER.19360690903
2-(3-hydroxypropyl)-1H-quinazolin-4-one	6325786	Click to see C1=CC=C2C(=C1)C(=O)N=C(N2)CCCO	204.22	unknown	https://doi.org/10.1007/BF00563655 https://doi.org/10.1007/BF00565223 https://doi.org/10.1007/BF00564251
3-Hydroxy-2,3-Dihydro-1H-Pyrrolo(2,1-B)Quinazolin-9-One	10242	Click to see	202.21	unknown	https://doi.org/10.1007/S10600-009-9381-3 https://doi.org/10.1007/S10600-006-0086-6
CID 776133	776133	Click to see C1CN2C(=NC3=CC=CC=C3C2=O)C1O	202.21	unknown	https://doi.org/10.1007/BF00564251 https://doi.org/10.1007/BF00567834 https://doi.org/10.1007/S10600-009-9381-3 https://doi.org/10.1007/BF00565223 https://doi.org/10.1007/S10600-006-0086-6
Deoxypeganine	442894	Click to see	172.23	unknown	https://doi.org/10.1007/BF00595109
Deoxyvasicinone	68261	Click to see	186.21	unknown	https://doi.org/10.1007/BF00563655 https://doi.org/10.1007/BF00564251 https://doi.org/10.1007/BF00567834 https://doi.org/10.1021/NP50018A025
Peganine	442929	Click to see	188.23	unknown	https://doi.org/10.1007/BF00563655 https://doi.org/10.1007/BF00564251 https://doi.org/10.1007/BF00567834 https://doi.org/10.1007/S10600-009-9381-3 https://doi.org/10.1007/BF00565223 https://doi.org/10.1007/BF00563370 https://doi.org/10.1016/S0021-9673(01)93059-6 https://doi.org/10.1002/CBER.19360690903 https://doi.org/10.1007/BF00579504 https://doi.org/10.1007/BF01373792 https://doi.org/10.1007/S10600-006-0086-6 https://doi.org/10.1007/BF00569029 https://doi.org/10.1007/BF00571245 https://doi.org/10.1021/NP50018A025
Pyrrolo(2,1-b)quinazoline-3,7-diol, 1,2,3,9-tetrahydro-, (R)-	6452262	Click to see C1CN2CC3=C(C=CC(=C3)O)N=C2C1O	204.22	unknown	via CMAUP database
> Organoheterocyclic compounds / Dihydrofurans / Furanones / Butenolides
L-Ascorbic Acid	54670067	Click to see	176.12	unknown	https://doi.org/10.1007/978-3-662-04480-3_6
> Organoheterocyclic compounds / Indoles and derivatives / Pyridoindoles / Beta carbolines
10-methoxy-2-methyl-7,12-dihydro-6H-indolo[2,3-a]quinolizin-4-one	14558296	Click to see	280.32	unknown	https://doi.org/10.3987/COM-89-4834
1H-Pyrido[3,4-b]indol-5-ol, 2,3,4,9-tetrahydro-	10375218	Click to see C1CNCC2=C1C3=C(N2)C=CC=C3O	188.23	unknown	https://doi.org/10.1016/0031-9422(93)85453-X
6-Hydroxy-1,2,3,4-tetrahydro-beta-carboline	159959	Click to see	188.23	unknown	https://doi.org/10.1016/0031-9422(93)85453-X
7-Methoxy-1,2,3,4-tetrahydropyrido[3,4-b]indole-9-carbaldehyde	14106930	Click to see	230.26	unknown	https://doi.org/10.3987/R-1987-06-1563
7-Methoxy-9-methyl-3,4-dihydropyrido[3,4-b]indole	118384447	Click to see	214.26	unknown	https://doi.org/10.1016/S0031-9422(00)86329-3
7-methoxy-9H-pyrido(3,4-b)indole	9815570	Click to see	198.22	unknown	https://doi.org/10.3987/COM-89-4834
Harmalacidine	179484	Click to see	216.24	unknown	https://doi.org/10.3987/R-1987-06-1563
Harmalidine	13819666	Click to see	254.33	unknown	https://doi.org/10.1016/S0031-9422(00)81861-0
Ojvcxvgfrrzmrp-uhfffaoysa-	14191996	Click to see	266.29	unknown	https://doi.org/10.3987/COM-88-4490 https://doi.org/10.3987/R-1987-06-1563
> Organoheterocyclic compounds / Indoles and derivatives / Tryptamines and derivatives
6-Hydroxytryptamine	160463	Click to see C1=CC2=C(C=C1O)NC=C2CCN	176.21	unknown	https://doi.org/10.1007/BF00563655 https://doi.org/10.1016/0031-9422(75)85054-0
> Organoheterocyclic compounds / Indoles and derivatives / Tryptamines and derivatives / Serotonins
Serotonin	5202	Click to see C1=CC2=C(C=C1O)C(=CN2)CCN	176.21	unknown	https://doi.org/10.1007/BF00563655 https://doi.org/10.1515/ZNC-1992-3-410 https://www.ncbi.nlm.nih.gov/pmc/articles/PMC426218/ https://doi.org/10.1016/0031-9422(93)85453-X https://doi.org/10.1016/0031-9422(75)85054-0
> Organoheterocyclic compounds / Piperidines
1-(3-Hydroxy-1,2,3,4,4a,8a-hexahydroisoquinolin-1-yl)propan-2-one	163035232	Click to see	207.27	unknown	https://doi.org/10.1007/BF00563655
1-[(1R,3S,4aR,8aS)-3-hydroxy-1,2,3,4,4a,8a-hexahydroisoquinolin-1-yl]propan-2-one	163035233	Click to see	207.27	unknown	https://doi.org/10.1007/BF00563655
> Organoheterocyclic compounds / Pyrrolidines / Phenylpyrrolidines
Vasicoline	626005	Click to see	291.40	unknown	via CMAUP database
> Organoheterocyclic compounds / Quinolines and derivatives
2-Methylquinoline	7060	Click to see	143.18	unknown	https://doi.org/10.1007/BF00563655
Quinoline	7047	Click to see	129.16	unknown	https://doi.org/10.1007/BF00563655
> Organoheterocyclic compounds / Quinolines and derivatives / Pyrroloquinolines
1,2,3,4-Tetrahydro-9h-pyrrolo[3,4-b]quinolin-9-one	12884011	Click to see	186.21	unknown	https://doi.org/10.1016/S0031-9422(00)86329-3
> Phenylpropanoids and polyketides / Flavonoids / Flavones / Flavonols
Kaempferol	5280863	Click to see	286.24	unknown	https://doi.org/10.1021/NP50032A022
Quercetin	5280343	Click to see	302.23	unknown	https://doi.org/10.1021/NP50032A022
> Phenylpropanoids and polyketides / Flavonoids / Flavonoid glycosides / Flavonoid C-glycosides / Flavonoid 8-C-glycosides
8-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one	102064906	Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)OC)O)O)CO)O)O)CO)O)O)O)O)O	754.70	unknown	https://doi.org/10.1016/S0031-9422(96)00531-6
8-[(2S,3R,4S,5S,6S)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one	162998076	Click to see	754.70	unknown	https://doi.org/10.1016/S0031-9422(96)00531-6
8-[3-[4,5-Dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one	74977544	Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)OC)O)O)CO)O)O)CO)O)O)O)O)O	754.70	unknown	https://doi.org/10.1016/S0031-9422(96)00531-6
Trematin	44257872	Click to see	446.40	unknown	https://doi.org/10.1016/S0031-9422(96)00531-6
> Phenylpropanoids and polyketides / Flavonoids / Flavonoid glycosides / Flavonoid O-glycosides / Flavonoid-7-O-glycosides
[(2S,3R,4R,5S,6S)-2-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl] acetate	102064904	Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)OC)O)COC6C(C(C(C(O6)CO)O)O)O)O)O)O)OC(=O)C)O	796.70	unknown	https://doi.org/10.1016/S0031-9422(96)00531-6
[(2S,3S,4R,5S,6S)-2-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-2-[5-hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl] acetate	162899284	Click to see	796.70	unknown	https://doi.org/10.1016/S0031-9422(96)00531-6
[2-[4,5-Dihydroxy-2-[5-hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl] acetate	74977553	Click to see	796.70	unknown	https://doi.org/10.1016/S0031-9422(96)00531-6
5-hydroxy-2-(4-methoxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one	102442676	Click to see	430.40	unknown	https://doi.org/10.1016/S0031-9422(96)00531-6
5-hydroxy-2-(4-methoxyphenyl)-7-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one	162906360	Click to see CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=CC3=O)C4=CC=C(C=C4)OC)O)O)O)O	430.40	unknown	https://doi.org/10.1016/S0031-9422(96)00531-6
7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one	162850281	Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4=CC(=C5C(=C4)OC(=CC5=O)C6=CC=C(C=C6)OC)O)CO)O)O)CO)O)O)O)O)O	754.70	unknown	https://doi.org/10.1016/S0031-9422(96)00531-6
7-[3-[4,5-Dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one	74977554	Click to see	754.70	unknown	https://doi.org/10.1016/S0031-9422(96)00531-6
Acacetin 7-O-[2'''-O-rhamnosyl-2''-O-glucosylglucoside	102064905	Click to see	754.70	unknown	https://doi.org/10.1016/S0031-9422(96)00531-6
Peganetin	5491743	Click to see	958.90	unknown	https://doi.org/10.1021/NP50050A028
> Phenylpropanoids and polyketides / Isoflavonoids / Isoflavonoid O-glycosides
7-[(2S,3R,4S,6S)-3,4-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-3-(4-methoxyphenyl)chromen-4-one	6325060	Click to see	560.50	unknown	via CMAUP database

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Peganum harmala

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