(3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-yl acetate hydrochloride

• ChemBase ID: 153867
• Molecular Formular: C23H32ClNO2
• Molecular Mass: 389.95868
• Monoisotopic Mass: 389.21215695
• SMILES: CC[C@@H](C(C[C@H](C)N(C)C)(c1ccccc1)c1ccccc1)OC(=O)C.Cl
• Canonical SMILES: CC[C@@H](C(c1ccccc1)(c1ccccc1)C[C@@H](N(C)C)C)OC(=O)C.Cl
• InChI: InChI=1S/C23H31NO2.ClH/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21;/h7-16,18,22H,6,17H2,1-5H3;1H/t18-,22-;/m0./s1
• InChIKey: UXBPQRGCVJOTNT-COBSGTNCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-yl acetate hydrochloride
• IUPAC Traditional name: levomethadyl acetate hydrochloride
• Synonyms: α-l-acetylmethadol hydrochloride; (1S)-2-[(2S)-2-(dimethylamino)propyl]-1-ethyl-2,2-diphenylethyl acetate hydrochloride; MK-790 hydrochloride; ORLAAM hydrochloride; levomethadyl acetate hydrochloride; α-1-Acetylmethadol hydrochloride; (αS)-β-[(2S)-2-(Dimethylamino)propyl]-α-ethyl-β-phenyl-benzeneethanol acetate (ester) hydrochloride hydrochloride; LAAM hydrochloride; (3S,6S)-(-)- 6-(Dimethylamino)-4,4-diphenyl-3-heptanol Acetate (Ester) Hydrochloride; (αS)-β-[(2S)-2-(Dimethylamino)propyl]-α-ethyl-β-phenylbenzeneethanol Acetate (Ester) Hydrochloride; (-)-6-(Dimethylamino)-4,4-diphenyl-3-heptanol Acetate (Ester) Hydrochloride; (-)-α-Acetylmethadol; Hydrochloride LAAM; Levacetylmethadol Hydrochloride; Levo-α-acetylmethadol Hydrochloride; Levomethadyl Hydrochloride; l-α-Acetylmethadol Hydrochloride; α-(-)-Acetylmethadol Hydrochloride; (-)-α-Acetylmethadol Hydrochloride; LAAM 盐酸盐

Database IDs

• CAS Number: 43033-72-3
• MDL Number: MFCD01723736
• PubChem SID: 162248006
• PubChem CID: 39371

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.4385403
• LogD (pH = 7.4): 2.4523962
• Log P: 4.8847694
• Molar Refractivity: 117.8576 cm^3
• Polarizability: 42.51397 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >5 mg/mL
• Apperance: white solid

Safety Information

• RTECS: MJ3680000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 25-36/37/38
• Safety Statements: 26-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H315-H319-H335-H413
• GHS Precautionary statements: P261-P264-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1
• Drug Control: USDEA Schedule II; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H32ClNO2

DETAILS

Sigma Aldrich - L7418

Other Notes
DEA Schedule II
Biochem/physiol Actions
LAAM hydrochloride is μ opioid receptor agonist. LAAM hydrochloride is a DEA-controlled substance, which has a slow onset, but a long duration of action. LAAM is a useful tool for studying opiate tolerance and cross-reactivity with other μ opioid receptor agonists.

Toronto Research Chemicals - A186325

The enantiomer of (+)-α-Acetylmethadol (A186320). A synthetic opioid similar in structure to Methadone (M225865) used in the treatment of opiate dependence. It acts as a μ-opioid receptor agonist. It also acts as a potent, noncompetitive α3β4 neuronal nic

REFERENCES

• Billings, R.E. et al.: Life Sci., 14, 1437 (1974)
• Galici, R. et al.: Pharmacol. Biochem. Behav., 81, 626 (1974)
• Xiao, Y. et al.: J. Pharmacol. Exp. Therap., 299, 366 (1974)