(-)-Heroin hydrochloride (CED0001244)

Record Information

Version

1.0

Creation Date

2016-05-22 06:48:49 UTC

Update Date

2026-04-05 16:02:47 UTC

Accession Number

CHEM020126

Identification

Common Name

(-)-Heroin hydrochloride

Class

Small Molecule

Description

(-)-Heroin hydrochloride belongs to the morphinans, a class of alkaloids and derivatives within the organic compounds. This compound has the formula C21H24ClNO5 and an average molecular weight of 405.87 g/mol.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Heroin hydrochloride	Kegg
Diamorphine	Kegg
Diamorphine hydrochloride	KEGG
(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 acetic acid hydrochloride	Generator
(1S,5R,13R,14S,17R)-14-(Acetyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0,.0,.0,]octadeca-7(18),8,10,15-tetraen-10-yl acetic acid hydrochloride	Generator

Chemical Formula

C₂₁H₂₄ClNO₅

Average Molecular Mass

405.872 g/mol

Monoisotopic Mass

405.134 g/mol

CAS Registry Number

1502-95-0

IUPAC Name

(1S,5R,13R,14S,17R)-10-(acetyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-yl acetate hydrochloride

Traditional Name

heroin hydrochloride

SMILES

Cl.[H][C@@]12OC3=C(OC(C)=O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@]2([H])OC(C)=O

InChI Identifier

InChI=1S/C21H23NO5.ClH/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;1H/t14-,15+,17-,20-,21-;/m0./s1

InChI Key

FZJYQGFGNHGSFX-PVQKIFDLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Morphinans

Sub Class

Not Available

Direct Parent

Morphinans

Alternative Parents

Substituents

Morphinan
Phenanthrene
Tetralin
Coumaran
Alkyl aryl ether
Aralkylamine
Dicarboxylic acid or derivatives
Piperidine
Benzenoid
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Ether
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Amine
Organic oxide
Carbonyl group
Organic chloride salt
Organic salt
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.27 g/L	ALOGPS
logP	2.3	ALOGPS
logP	1.55	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	9.1	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	98.43 m³·mol⁻¹	ChemAxon
Polarizability	38.52 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0000900000-5655f160000137dffe9a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0000900000-5655f160000137dffe9a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0000900000-5655f160000137dffe9a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0000900000-3a77eb84ce384c1eaf3c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0000900000-3a77eb84ce384c1eaf3c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0000900000-3a77eb84ce384c1eaf3c	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
246.0	Log mg/kg	[140:440]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	63.6807
Click to view 3D structure	Kappa-type opioid receptor	P41144	Cavia porcellus	Predicted (SEA)	57.1413
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	91.7842
Click to view 3D structure	Mu-type opioid receptor	P97266	Cavia porcellus	Predicted (SEA)	104.084
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	143.865
Click to view 3D structure	Mu-type opioid receptor	P42866	Mus musculus	Predicted (SEA)	60.8002
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	155.231
Click to view 3D structure	Delta-type opioid receptor	P32300	Mus musculus	Predicted (SEA)	173.837
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	165.196
Click to view 3D structure	Mas-related G-protein coupled receptor member X2	Q96LB1	Humans	Predicted (SEA)	79.9511
Click to view 3D structure	Delta-type opioid receptor	P33533	Rattus norvegicus	Predicted (SEA)	177.73
Click to view 3D structure	Kappa-type opioid receptor	P33534	Mus musculus	Predicted (SEA)	90.3051
Click to view 3D structure	Nociceptin receptor	P47748	Cavia porcellus	Predicted (SEA)	13.0787
Click to view 3D structure	Kappa-type opioid receptor	P34975	Rattus norvegicus	Predicted (SEA)	164.106
Click to view 3D structure	Mu-type opioid receptor	P79350	Bos taurus	Predicted (SEA)	17.8275
Click to view 3D structure	Nociceptin receptor	P41146	Humans	Predicted (SEA)	199.917
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	855.719
Click to view 3D structure	Acetylcholinesterase	O42275	Electrophorus electricus	Predicted (SEA)	506.721
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Predicted (SEA)	981.134
Click to view 3D structure	Orexin/Hypocretin receptor type 1	O43613	Humans	Predicted (SEA)	115.762
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	3492.47
Click to view 3D structure	Opioid receptor homologue	A3QJX7	Danio rerio	Predicted (SEA)	27.3251
Click to view 3D structure	Acetylcholinesterase	P04058	Torpedo californica	Predicted (SEA)	125.337
Click to view 3D structure	Acetylcholinesterase	P37136	Rattus norvegicus	Predicted (SEA)	538.872
Click to view 3D structure	Cholinesterase	P81908	Equus caballus	Predicted (SEA)	1220.21