Diacetylmorphine (Heroin)

Heroin

Molecular structure via molpic based on CDK

Conformer []

Conformer structure via JSmol

Physical properties []
Molecular mass	369.4 g/mol ^[1]
Density	1.56 g/cu m at 25 °C g/cm³ ^[1]
Appearance	Orthorhombic plates, tablets from ethyl acetate ^[1]
Odor	Odorless ^[1]
Taste	Bitter ^[1]
Melting point	173 °C ^[1]
Boiling point	272-274 °C at 1.20E+01 mm Hg ^[1]
Decomposition	... Decomposes by boiling with water. ^[1]
Solubility	In water, 60 mg/L at 25 °C ^[1]
Predicted LogP	1.5 ^[1]

Structural Identifiers []
Molecular formula	C₂₁H₂₃NO₅ ^[1]
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 ^[1]
SMILES	CC(=O)O[C@H]1C=C[C@H]2[C@H]3CC4=C5[C@]2([C@H]1OC5=C(C=C4)OC(=O)C)CCN3C ^[1]
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 ^[1]
InChIKey	GVGLGOZIDCSQPN-PVHGPHFFSA-N ^[1]

Diacetylmorphine

Diacetylmorphine (also known as HEROIN, Diamorphine, Acetomorphine, 3,6-Diacetylmorphine, Diaphorm, Eclorion, Morphacetin, O,O'-Diacetylmorphine, Morphine diacetate or Acetomorfine) is a prodrug and opioid substance of the morphinan class.

Chemistry

Active metabolites []
Morphine 6-Monoacetylmorphine

Physical effects
Constipation Cough suppression Difficulty urinating Itchiness Nausea Pain relief Pupil constriction Respiratory depression Sedation Stomach cramp

Cognitive effects
Anxiety suppression Cognitive euphoria Compulsive redosing Increased music appreciation Thought deceleration

Visual effects
Double vision

Anodyne Usernotes []
0xea / Diacetylmorphine^{[citrate][ascorbate]} via Vaporized and Intravenous	<a href=/class/prodrug>Prodrug</a> to 6-Monoacetylmorphine; not very classy

References []

National Center for Biotechnology Information. PubChem Compound Summary for CID 5462328, Diacetylmorphine. Accessed July 19, 2025. https://pubchem.ncbi.nlm.nih.gov/compound/5462328
U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Diacetylmorphine. UNII: 70D95007SX. Global Substance Registration System. Accessed July 19, 2025. https://gsrs.ncats.nih.gov/ginas/app/beta/substances/70D95007SX

Anodyne

Diacetylmorphine

Chemistry

Stereochemistry []

Pharmacology

Subjective effects []

See also []

External links []

References []