Heroin

Details

• Internal ID: 6e2e724b-ed39-441d-934c-f58261bafcf5
• Taxonomy: Alkaloids and derivatives > Morphinans
• IUPAC Name: [(4R,4aR,7S,7aR,12bS)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] acetate
• InChI: InChI=1S/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1
• InChI Key: GVGLGOZIDCSQPN-PVHGPHFFSA-N
• Popularity: 25,368 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.40 g/mol
• Exact Mass: 369.15762283 g/mol
• Topological Polar Surface Area (TPSA): 65.10 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.99
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• Diacetylmorphine
• Diamorphine
• Acetomorphine
• 3,6-Diacetylmorphine
• Diaphorm
• Eclorion
• Morphacetin
• O,O'-Diacetylmorphine
• Morphine diacetate
• 561-27-3
• Acetomorfine
• Diacetylmorfin
• Diamorfina
• Diasetilmorfin
• Diacephin
• Diasetielmorfien
• Diasetylmorfiimi
• Diazetylmorphine
• Diacetyl morphine
• 3,6-O-Diacetylmorphine
• 7,8-Dihydro-4,5-alpha-epoxy-17-methylmorphinan-3,6-alpha-diol diacetate
• IDS-NH-001
• DTXSID6046761
• CHEBI:27808
• IDS-NH-001(SECT.3)
• 70D95007SX
• J6.494G
• 7,8-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol diacetate (ester)
• (5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol diacetate (ester)
• DTXCID4026761
• Morphinan-3,6-alpha-diol, 7,8-didehydro-4,5-alpha-epoxy-17-methyl-, diacetate (ester)
• Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl-, (5alpha,6alpha)-, diacetate (ester)
• 17-methyl-7,8-didehydro-4,5alpha-epoxymorphinan-3,6alpha-diyl diacetate
• [(4R,4aR,7S,7aR,12bS)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] acetate
• Diamorf
• ((4R,4aR,7S,7aR,12bS)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinolin-7-yl) acetate
• ((4R,4aR,7S,7aR,12bS)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinoline-7-yl) acetate
• [(4R,4aR,7S,7aR,12bS)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-yl] acetate
• Hydrochloride, Heroin
• RefChem:783762
• Min I Jet Morphine Sulphate
• Hydrochloride, Diacetylmorphine
• (1S,5R,13R,14S,17R)-14-(acetyloxy)-4-methyl-12-oxa-4-azapentacyclo(9.6.1.01,13.05,17.07,18)octadeca-7(18),8,10,15-tetraen-10-yl acetate
• 209-217-7
• Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl-(5alpha,6alpha)-, diacetate (ester)
• Preza
• Aspron
• Eroina
• Heroien
• Heroiin
• Herolan
• Iroini
• Persian
• Dooje
• Dujie
• Stuff
• Junk
• Scot
• Amsterdam Marble
• TNT (narcotic)
• HSDB 6473
• Hairy
• Harry
• White stuff
• JOY POWDER
• Acetomorphin
• Smack
• Rufus
• Crap
• Persian brown
• Malaysian Pink
• Mexican Brown
• White junk
• Black tar
• Heroin (Diacetylmorphine)
• Indian Pink
• Penang Pink
• Heroin (3,6-Diacetylmorphine)
• Scag
• Heroin (1.0 mg/mL in Acetonitrile)
• Boy [Street Name]
• Crap [Street Name]
• Scag [Street Name]
• Hairy [Street Name]
• Harry [Street Name]
• Horse [Street Name]
• Noise [Street Name]
• Rufus [Street Name]
• Smack [Street Name]
• BOY
• EINECS 209-217-7
• Joy powder [Street Name]
• White stuff [Street Name]
• Black tar [Street Name]
• Indian Pink [Street Name]
• Penang Pink [Street Name]
• White junk [Street Name]
• Persian brown [Street Name]
• Mexican Brown [Street Name]
• Malaysian Pink [Street Name]
• DEA No. 9200
• UNII-70D95007SX
• Diamorphine (BAN)
• DIAMORPHINE-
• HEROIN [HSDB]
• Diacetylmorphine (Heroin)
• NCGC00168253-01
• SCHEMBL35150
• DIACETYLMORPHINE [MI]
• DIAMORPHINE [WHO-DD]
• CHEMBL459324
• GTPL9082
• 3,6-Diacetylmorphine (Heroin)
• SCHEMBL29631710
• GVGLGOZIDCSQPN-PVHGPHFFSA-N
• (5.alpha.,6.alpha.)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol diacetate (ester)
• Tox21_112612
• DB01452
• CAS-561-27-3
• DB-220304
• NS00000040
• Heroin, analytical standard, >=98% (HPLC)
• C06534
• D07286
• Q60168
• Heroin (Diacetylmorphine) 1.0 mg/ml in Acetonitrile
• Heroin (3,6-Diacetylmorphine), 1mg/ml in Acetonitrile
• morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl-, diacetate (ester), (5alpha,6alpha)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9704	97.04%
Caco-2	+	0.6402	64.02%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.9571	95.71%
Subcellular localzation	Mitochondria	0.4401	44.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9224	92.24%
OATP1B3 inhibitior	+	0.9285	92.85%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5360	53.60%
P-glycoprotein inhibitior	+	0.6187	61.87%
P-glycoprotein substrate	+	0.6963	69.63%
CYP3A4 substrate	+	0.7438	74.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3642	36.42%
CYP3A4 inhibition	-	0.8072	80.72%
CYP2C9 inhibition	-	0.8162	81.62%
CYP2C19 inhibition	-	0.8059	80.59%
CYP2D6 inhibition	-	0.6335	63.35%
CYP1A2 inhibition	-	0.7994	79.94%
CYP2C8 inhibition	-	0.9265	92.65%
CYP inhibitory promiscuity	-	0.8335	83.35%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5810	58.10%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9721	97.21%
Skin irritation	-	0.8024	80.24%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.7254	72.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7260	72.60%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8478	84.78%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.6375	63.75%
Acute Oral Toxicity (c)	III	0.7187	71.87%
Estrogen receptor binding	+	0.5939	59.39%
Androgen receptor binding	-	0.6642	66.42%
Thyroid receptor binding	-	0.5614	56.14%
Glucocorticoid receptor binding	+	0.7398	73.98%
Aromatase binding	-	0.6610	66.10%
PPAR gamma	+	0.6508	65.08%
Honey bee toxicity	-	0.6304	63.04%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5550	55.50%
Fish aquatic toxicity	+	0.9758	97.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.37%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.57%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.61%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.47%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.73%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.97%	86.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.77%	100.00%
CHEMBL217	P14416	Dopamine D2 receptor	83.83%	95.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.05%	94.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	82.27%	90.95%
CHEMBL340	P08684	Cytochrome P450 3A4	81.88%	91.19%
CHEMBL3474	P14555	Phospholipase A2 group IIA	81.34%	94.05%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.91%	100.00%
CHEMBL5028	O14672	ADAM10	80.60%	97.50%

Plants that contains it

• Papaver somniferum

Cross-Links

• PubChem: 5462328
• NPASS: NPC311781