(1S,5R,13R,14S,17R)-14-(acetyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18),15-tetraen-10-yl acetate

• ChemBase ID: 127670
• Molecular Formular: C21H23NO5
• Molecular Mass: 369.41102
• Monoisotopic Mass: 369.15762284
• SMILES: CC(=O)Oc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4C=C[C@@H]1OC(=O)C)C
• Canonical SMILES: CC(=O)O[C@H]1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1OC(=O)C
• 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
• InChIKey: GVGLGOZIDCSQPN-PVHGPHFFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14S,17R)-14-(acetyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18),15-tetraen-10-yl acetate
• IUPAC Traditional name: (1S,5R,13R,14S,17R)-14-(acetyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18),15-tetraen-10-yl acetate
• Synonyms: Heroin; Diamorphine; Diacetylmorphine; Acetomorphine; (Dual) Acetylated morphine; Morphine diacetate; Heroin; 二乙酰吗啡; 海洛因

Database IDs

• CAS Number: 561-27-3
• EC Number: 209-217-7
• MDL Number: MFCD00468072
• PubChem SID: 162221988; 24895466
• PubChem CID: 5462328
• CHEBI ID: 27808
• ATC CODE: N07BC06
• CHEMBL: 459324
• Chemspider ID: 4575379
• DrugBank ID: DB01452
• Unique Ingredient Identifier: 8H672SHT8E
• Wikipedia Title: Heroin

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -1.697644
• LogD (pH = 7.4): -0.152045
• Log P: 1.549009
• Molar Refractivity: 98.4254 cm^3
• Polarizability: 38.45062 Å^3
• Polar Surface Area: 65.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: <6.67 mg/mL; ethanol: soluble6 mg/mL; H2O: <0.2 mg/mL
• Apperance: solid

Safety Information

• Storage Condition: desiccated
• RTECS: QC8050000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28
• Safety Statements: 22-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 1
• Drug Control: USDEA Schedule I; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Admin Routes: Inhalation, Transmucosal, Intravenous, Oral, Intranasal, Rectal, Intramuscular
• Bioavailability: <35% (oral), 44–61% (inhaled)
• Dependency Liability: High
• Excretion: 90% renal as glucuronides, rest biliary
• Half Life: <10 minutes
• Metabolism: hepatic
• Protein Bound: 0% (morphine metabolite 35%)
• Legal Status: Class A (UK); S9 (Australia); Schedule I (Canada); Schedule I (US)
• Pregnancy Category: Not yet classified, but studies have shown a risk of abnormalities, hepatitis, malnutrition, and many other effects.

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H23NO5