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

• ChemBase ID: 153562
• Molecular Formular: C19H21NO4
• Molecular Mass: 327.37434
• Monoisotopic Mass: 327.14705816
• SMILES: CC(=O)O[C@H]1C=C[C@H]2[C@H]3Cc4ccc(c5c4[C@]2([C@H]1O5)CCN3C)O
• Canonical SMILES: CC(=O)O[C@H]1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1O
• InChI: InChI=1S/C19H21NO4/c1-10(21)23-15-6-4-12-13-9-11-3-5-14(22)17-16(11)19(12,18(15)24-17)7-8-20(13)2/h3-6,12-13,15,18,22H,7-9H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1
• InChIKey: JJGYGPZNTOPXGV-SSTWWWIQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14S,17R)-10-hydroxy-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-14-yl acetate
• IUPAC Traditional name: monoacetylmorphine
• Synonyms: 6-Acetylmorphine solution; MAM; Monoacetylmorphine; Morphine 6-acetate hydrochloride; O6单乙酰吗啡 溶液; 单乙酰吗啡; 6-乙酸吗啡 盐酸盐

Database IDs

• CAS Number: 2784-73-8
• MDL Number: MFCD00467140
• PubChem SID: 162247701
• PubChem CID: 5462507

CALCULATED PROPERTIES

• Polarizability: 34.61431 Å^3
• Polar Surface Area: 59.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 10.187711
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.638114
• LogD (pH = 7.4): -0.13188331
• Log P: 1.3072112
• Molar Refractivity: 89.2739 cm^3

PROPERTIES

Safety Information

• RTECS: QC7814500
• European Hazard Symbols: Highly toxic (T+); Harmful (Xn)
• UN Number: 1544; 1648
• German water hazard class: 2; 3
• Hazard Class: 3; 6.1
• Packing Group: 2
• Risk Statements: 20/21/22-36; 26/27/28
• Safety Statements: 22-36/37/39-45; 26-36/37
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330; H302-H312-H319-H331
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350; P261-P280-P305 + P351 + P338-P311
• 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; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1544 6.1/PG 2; UN 1648 3/PG 2
• Drug Control: kontrollierte Droge in Deutschlandregulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%
• Concentration: 1 mg/mL in acetonitrile
• Grade: analytical standard, for drug analysis
• Empirical Formula (Hill Notation): C19H21NO4; C19H21NO4 · HCl

DETAILS

Sigma Aldrich - M5913

Biochem/physiol Actions
Narcotic analgesic; more lipid soluble than morphine which enhances uptake into brain where it is converted to morphine