Epinephrine

Details

• Internal ID: 7d6aa7cd-bdb3-43dc-a941-666f30e540e8
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols
• IUPAC Name: 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
• SMILES (Canonical): CNCC(C1=CC(=C(C=C1)O)O)O
• SMILES (Isomeric): CNC[C@@H](C1=CC(=C(C=C1)O)O)O
• InChI: InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1
• InChI Key: UCTWMZQNUQWSLP-VIFPVBQESA-N
• Popularity: 138,704 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₃NO₃
• Molecular Weight: 183.20 g/mol
• Exact Mass: 183.08954328 g/mol
• Topological Polar Surface Area (TPSA): 72.70 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): 0.35
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• l-Adrenaline
• adrenaline
• L-epinephrine
• 51-43-4
• Adrenalin
• Levoepinephrine
• Nephridine
• Adnephrine
• Chelafrin
• Epinefrina
• Epinephran
• Epirenan
• Epipen
• (-)-Epinephrine
• (-)-Adrenaline
• Renoform
• Epifrin
• Vasoconstrictine
• Bronkaid Mist
• Primatene Mist
• Sus-Phrine
• Adrenalinum
• Glauposine
• Hemostasin
• Hemostatin
• Hypernephrin
• Levorenin
• Levorenine
• Mucidrina
• Nieraline
• Paranephrin
• Renaglandin
• Renaleptine
• Renostypticin
• Scurenaline
• Styptirenal
• Supracapsulin
• Supranephrane
• Vasotonin
• Adrenal
• Adrenine
• Exadrin
• Hemisine
• Lyophrin
• Renalina
• Simplene
• Takamina
• Twinject
• Adrin
• Bosmin
• (R)-Adrenaline
• l-Epirenamine
• (-)-(R)-Epinephrine
• Antiasthmatique
• Esphygmogenina
• Isoptoepinal
• Methylarterenol
• Sphygmogenin
• Stryptirenal
• Supranephrine
• Adrenamine
• Adrenapax
• Adrenasol
• Adrenodis
• Adrenohorma
• Adrenosan
• Adrenutol
• Astmahalin
• Astminhal
• Balmadren
• Bernarenin
• Biorenine
• Brevirenin
• Bronkaid
• Drenamist
• Dylephrin
• Glaucosan
• Glycirenan
• Haemostasin
• Haemostatin
• Hektalin
• Hyporenin
• Intranefrin
• Kidoline
• Myosthenine
• Sindrenina
• Soladren
• Supranefran
• Supranol
• Takamine
• Tokamina
• Vasodrine
• Corisol
• Mytrate
• Suprel
• Tonogen
• Asthma-nefrin
• Asmatane Mist
• Sympathin I
• (R)-Epinephrine
• Asthma meter mist
• Supradin
• Glaucon
• Adrenalin-Medihaler
• Dyspne-Inhal
• 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
• R-(-)-Epinephrine
• Epiglaufrin
• Epinephrinum
• Epinefrin
• Levorenen
• Susphrine
• 1-Epinephrine
• 1-Adrenalin
• Epipen Jr.
• Epinefrin [Czech]
• Renaglandulin
• Renostypricin
• Vasoconstrictor
• Adrenalina
• Adrenatrate
• Epirenin
• Metanephrin
• Renagladin
• Renostyptin
• Surenine
• Surrenine
• Vaponefrin
• (R)-(-)-Adrenaline
• Vasoton
• Rcra waste number P042
• l-Adrenalin
• l-Epinephrine (synthetic)
• R-Adrenaline
• Auvi-q
• Methylaminoethanolcatechol
• (R)-(-)-Epinephrine
• L(-)-Epinephrine
• Adrenalina [DCIT]
• Adrenaclick
• Epinefrina [INN-Spanish]
• Epinephrinum [INN-Latin]
• l-Methylaminoethanolcatechol
• Lyodrin
• Symjepi
• Eppy
• (R)-(-)-Adnephrine
• EPIPEN E Z PEN
• SUS-PHRINE SULFITE-FREE
• (R)-(-)-Epirenamine
• EPI E Z PEN JR
• Twinject 0.3
• l-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol
• Auvi-Q auto-injector
• Twinject 0.15
• Racepinefrine, (r)-
• EPIPEN JR
• d-Adrenaline
• 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (R)-
• Epinephrin
• Levoreninum
• CCRIS 4812
• Anapen
• Sus-phrine sulphite-free
• L-Epinehphrine
• HSDB 4289
• (-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol
• AI3-19015
• RCRA waste no. P042
• UNII-YKH834O4BH
• Ana-Kit
• 4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol
• EINECS 200-098-7
• Adrenalin (TN)
• Micronefrin
• NSC 62786
• Adrenan
• Adrine
• Levo-Methylaminoethanolcatechol
• 4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol
• Epinephrine hydrochloride
• 1-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol
• Epinephrine [USAN:INN:JAN]
• (-)-R-Epinephrine
• DTXSID5022986
• Lopac-E-4642
• 1,2-Benzenediol, 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-
• NSC-62786
• CHEMBL679
• YKH834O4BH
• C9H13NO3
• l-Epinephine
• D-Epinephrine
• (R)-4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol
• DTXCID802986
• Asthmahaler Mist
• Bupivacaine Hcl and Epinephrine
• Ana-Guard
• D-Epifrin
• CHEBI:28918
• Epipen EZ Pen
• L-Adrenaline Base
• 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (theta)-
• Benzyl alcohol, 3,4-dihydroxy-alpha-((methylamino)methyl)-, (-)-
• Epinephrine [USP:INN:BAN:JAN]
• (-)-Adrenalin
• Epi EZ Pen Jr
• ADROP
• Epipen Auto-Injector
• OCTOCAINE COMPONENT EPINEPHRINE
• IONTOCAINE COMPONENT EPINEPHRINE
• NCGC00015417-01
• NCGC00142615-03
• NCGC00142615-08
• EPINEPHRINE COMPONENT OF OCTOCAINE
• EPINEPHRINE COMPONENT OF IONTOCAINE
• 1,2-Benzenediol, 4-((1R)-1-hydroxy-2-(methylamino)ethyl)-
• Bronkaid Suspension Mist
• Epipen Jr. Auto-Injector
• ADRENALINE (MART.)
• ADRENALINE [MART.]
• Primatene
• rac Epinephrine
• ADRENALINE (EP IMPURITY)
• ADRENALINE [EP IMPURITY]
• LIDOSITE TOPICAL SYSTEM KIT COMPONENT EPINEPHRINE
• (-)-3,4-Dihydroxy-a-[2-(methylamino)ethyl]benzyl alcohol
• ADRENALINE (EP MONOGRAPH)
• ADRENALINE [EP MONOGRAPH]
• EPINEPHRINE COMPONENT OF LIDOSITE TOPICAL SYSTEM KIT
• Exadri
• EPINEPHRINE (USP MONOGRAPH)
• EPINEPHRINE [USP MONOGRAPH]
• 1,2-Benzenediol, 4-[1-hydroxy-2-(methylamino)ethyl]-, (R)-
• Alipogene tiparvovec
• Epinephrine (USP)
• 4-((1R)-1-HYDROXY-2-(METHYLAMINO)ETHYL)-1,2-BENZENEDIOL
• Epipen (TN)
• Twinject 0.30
• Adrenaline/Epinephrine
• Adrenaline (JP15)
• CAS-51-43-4
• Epinephrine (USP/INN)
• NORADRENALINE TARTRATE IMPURITY A (EP IMPURITY)
• NORADRENALINE TARTRATE IMPURITY A [EP IMPURITY]
• (r)-4-(1-hydroxy-2-(methylamino)ethyl)benzene-1,2-diol
• adrenina
• epifrina
• (R)-4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol
• 4-((1R)-1-hydroxy-2-(methylamino)ethyl)benzene-1,2-diol
• adrAnaline
• Glauposina
• Hypernefrin
• Suprarrenal
• Adnefrine
• Epinefran
• Hemisina
• (-)-3,4-dihydroxy-alpha-[(methylamino)methyl]benzyl alcohol
• Bronkaid niebla
• epinephrin-
• NSC62786
• Benzyl alcohol, 3,4-dihydroxy-.alpha.-[(methylamino)methyl]-, (-)-
• (R)-adrenalina
• (R)-epinefrina
• BENZYL ALCOHOL, 3,4-DIHYDROXY-.ALPHA.-((METHYLAMINO)METHYL)-, (-)-
• (-)-Adrenalina
• epinephrine solution
• ALE
• IOP
• nchembio747-comp9
• ASTHMAHALIN
• Adrenaline (JP17)
• Epitrate (Salt/Mix)
• Auvi-q (TN)
• epinephrine|racepinefrine
• ADRENALINE [JAN]
• EPINEPHRINE [MI]
• 4-(1-hydroxy-2-methylamino-ethyl)benzene-1,2-diol
• EPINEPHRINE [INN]
• (-)-( R)-adrenalina
• (-)-( R)-epinefrina
• ADRENALINUM [HPUS]
• EPINEPHRINE [HSDB]
• bmse000316
• 4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol #
• Citanest Forte (Salt/Mix)
• L-Adrenaline (Epinephrine)
• SCHEMBL3814
• 3,4-Dihydroxy-.alpha.-((methylamino)methyl)benzyl alcohol
• EPINEPHRINE [USP-RS]
• EPINEPHRINE [WHO-DD]
• EPINEPHRINE [WHO-IP]
• GTPL479
• BIDD:GT0119
• E4250_SIGMA
• SUS-PHRINE SULFITE FREE
• EPINEPHRINE (COPACKAGED)
• (-)-Epinephrine (+)-bitartrate salt;L-Adrenaline (+)-bitartrate salt
• BDBM44818
• cid_6852374
• HY-B0447B
• A01AD01
• B02BC09
• C01CA24
• component of E-Pilo (Salt/Mix)
• EPINEPHRINE (AUTOINJECTOR)
• EPINEPHRINE [ORANGE BOOK]
• R01AA14
• R03AA01
• S01EA01
• HMS3884H06
• 104655-05-2
• 929881-05-0
• BCP09042
• EPINEPHRINUM [WHO-IP LATIN]
• Tox21_111562
• BDBM50029050
• HSCI1_000215
• LS-156
• PDSP1_001120
• PDSP2_001104
• s2522
• 51-43-4 (FREE BASE)
• AKOS024283500
• Tox21_111562_1
• CCG-204593
• DB00668
• SDCCGSBI-0050486.P002
• SMP1_000227
• (-)-Epinephrine, >=97.0% (NT)
• NCGC00142615-01
• NCGC00142615-04
• NCGC00142615-05
• NCGC00142615-06
• NCGC00142615-07
• NCGC00142615-09
• NCGC00142615-18
• AC-13188
• AC-31211
• AS-13813
• 4,5-beta-trihydroxy-N-methylphenethylamine
• A0173
• SW219274-1
• (-)-Epinephrine;L-Adrenaline;(-)-Adrenalin
• C00788
• D00095
• D88222
• EN300-120880
• AB00573227-11
• AB00573227-12
• AB00573227-13
• AB00573227_14
• AB00573227_15
• Q132621
• Q-200601
• SR-01000075267-8
• 4-[(1R)-1-hydroxy-2-methylaminoethyl]benzene-1,2-diol
• Z1255449978
• (-)-3,4-dihydroxy-a-[(methylamino)methyl]-Benzyl alcohol
• 12-Benzenediol 4-[1-hydroxy-2-(methylamino)ethyl]-(R)-
• Adrenaline, European Pharmacopoeia (EP) Reference Standard
• (-)-3 4-Dihydroxy-alpha-[2-(methylamino)ethyl]benzyl alcohol
• (-)-3,4-dihydroxy-alpha-[(methylamino)methyl]-Benzyl alcohol
• (-)-3,4-Dihydroxy-alpha-[2-(methylamino)ethyl]benzyl alcohol
• 1,2-Bencenodiol, 4-[(1R)-1-hidroxi-2-(metilamino) etil]-
• 1,2-bencenodiol, 4-[1-hidroxi-2-(metilamino) etil]-, (R)-
• 1,2-bencenodiol, 4-[1-hidroxi-2-(metilamino) etil]-,(R)-
• 1,2-Benzenediol, 4-[1-hidroxi-2-(metilamino) etil]-,(R)
• 1,2-BENZENEDIOL,4-(1-HYDROXY-2-(METHYLAMINO)ETHYL)-
• 3,4-DIHYDROXY-1-(1-HYDROXY-2-(METHYLAMINO)ETHYL)BENZENE
• 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]pyrocatechol;tartaric acid
• Benzyl alcohol34-dihydroxy-alpha-[(methylamino)methyl]-(-)-(8CI)
• (-)-3,4-DIHYDROXY-.ALPHA.-((METHYLAMINO)METHYL)BENZYL ALCOHOL
• Adrenaline with impurity F, European Pharmacopoeia (EP) Reference Standard
• EPINEPHRINE (SEE ALSO: EPINEPHRINE HYDROCHLORIDE (CAS 55-31-2))
• 2,3-dihydroxybutanedioic acid;4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
• Epinephrine; (Vasotonin; (R)-4-(1-hydroxy-2-(methylamino)ethyl)-1,2-Benzenediol)
• 2,3-bis(oxidanyl)butanedioic acid;4-[(1R)-2-(methylamino)-1-oxidanyl-ethyl]benzene-1,2-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9802	98.02%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7131	71.31%
OATP2B1 inhibitior	-	0.8625	86.25%
OATP1B1 inhibitior	+	0.9457	94.57%
OATP1B3 inhibitior	+	0.9588	95.88%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9880	98.80%
P-glycoprotein inhibitior	-	0.9810	98.10%
P-glycoprotein substrate	-	0.9363	93.63%
CYP3A4 substrate	-	0.7865	78.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5000	50.00%
CYP3A4 inhibition	-	0.9121	91.21%
CYP2C9 inhibition	-	0.9563	95.63%
CYP2C19 inhibition	-	0.9451	94.51%
CYP2D6 inhibition	-	0.9638	96.38%
CYP1A2 inhibition	-	0.7862	78.62%
CYP2C8 inhibition	-	0.9609	96.09%
CYP inhibitory promiscuity	-	0.9516	95.16%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8108	81.08%
Carcinogenicity (trinary)	Non-required	0.7037	70.37%
Eye corrosion	-	0.8952	89.52%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.6097	60.97%
Skin corrosion	-	0.6947	69.47%
Ames mutagenesis	-	0.9800	98.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6998	69.98%
Micronuclear	-	0.6968	69.68%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.5367	53.67%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8507	85.07%
Acute Oral Toxicity (c)	II	0.5282	52.82%
Estrogen receptor binding	-	0.8012	80.12%
Androgen receptor binding	-	0.7439	74.39%
Thyroid receptor binding	-	0.5318	53.18%
Glucocorticoid receptor binding	-	0.6491	64.91%
Aromatase binding	-	0.8033	80.33%
PPAR gamma	-	0.9017	90.17%
Honey bee toxicity	-	0.8548	85.48%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.8636	86.36%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	14125.4 nM	Potency	via CMAUP
CHEMBL229	P35348	Alpha-1a adrenergic receptor	400 nM	EC50	PMID: 2845082
CHEMBL232	P35368	Alpha-1b adrenergic receptor	75 nM	EC50	via Super-PRED
CHEMBL223	P25100	Alpha-1d adrenergic receptor	449 nM	IC50	via CMAUP
CHEMBL1867	P08913	Alpha-2a adrenergic receptor	737 nM	IC50	via CMAUP
CHEMBL1942	P18089	Alpha-2b adrenergic receptor	869 nM	IC50	via CMAUP
CHEMBL1916	P18825	Alpha-2c adrenergic receptor	2449 nM	IC50	via CMAUP
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	28183.8 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	17782.8 nM; 112201.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL213	P08588	Beta-1 adrenergic receptor	290 nM	EC50	via Super-PRED
CHEMBL210	P07550	Beta-2 adrenergic receptor	284 nM; 360 nM	IC50; Ki	via CMAUP; via Super-PRED
CHEMBL246	P13945	Beta-3 adrenergic receptor	31 nM; 31 nM; 49 nM	EC50; EC50; EC50	PMID: 18083578; via Super-PRED; PMID: 18083578
CHEMBL3356	P05177	Cytochrome P450 1A2	15848.93 nM	AC50	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	39810.7 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL217	P14416	Dopamine D2 receptor	910 nM; 910 nM	Ki; Ki	via Super-PRED; PMID: 27132867
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	794.3 nM; 794.3 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	1584.9 nM; 1584.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	7079.5 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	3981.1 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	12589.3 nM; 7943.3 nM; 11220.2 nM; 14125.4 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	23280.9 nM; 26121.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	3162.3 nM; 794.3 nM; 3548.1 nM	Potency; Potency; Potency	via CMAUP; via Super-PRED; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.10%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.97%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.35%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.22%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	88.58%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.78%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	87.11%	94.73%
CHEMBL4208	P20618	Proteasome component C5	87.09%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.15%	94.45%

Plants that contains it

• Aruncus dioicus
• Buxus sempervirens
• Crataegus laevigata
• Dysoxylum lenticellatum
• Hemidesmus indicus
• Hesperocyparis macrocarpa
• Isocoma veneta
• Kochia trichophylla
• Leuzea carthamoides
• Petchia madagascariensis
• Piper kadsura
• Portulaca grandiflora
• Potentilla multifida
• Psephellus trinervius
• Saururus cernuus
• Scoparia dulcis
• Seriphidium oranense
• Strychnos fendleri
• Vicia villosa
• Vitex megapotamica

Cross-Links

• PubChem: 5816
• NPASS: NPC236347
• ChEMBL: CHEMBL679
• LOTUS: LTS0235972
• wikiData: Q132621