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L7418

Sigma-Aldrich

LAAM hydrochloride

≥98% (HPLC), solid

Synonym(s):

α-1-Acetylmethadol hydrochloride, (αS)-β-[(2S)-2-(Dimethylamino)propyl]-α-ethyl-β-phenyl-benzeneethanol acetate (ester) hydrochloride hydrochloride, Levomethadyl acetate hydrochloride, MK-790 hydrochloride, ORLAAM hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C23H32ClNO2
CAS Number:
Molecular Weight:
389.96
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:

Assay

≥98% (HPLC)

form

solid

drug control

USDEA Schedule II; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

color

white

solubility

H2O: >5 mg/mL

storage temp.

2-8°C

SMILES string

Cl.CC[C@H](OC(C)=O)C(C[C@H](C)N(C)C)(c1ccccc1)c2ccccc2

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

InChI key

UXBPQRGCVJOTNT-COBSGTNCSA-N

Gene Information

human ... OPRM1(4988)

Biochem/physiol Actions

LAAM hydrochloride is μ opioid receptor agonist.
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.

Other Notes

DEA Schedule II

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 2 Oral - Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Erich F Wedam et al.
Archives of internal medicine, 167(22), 2469-2475 (2007-12-12)
Levomethadyl acetate, methadone hydrochloride, and buprenorphine hydrochloride are equally effective treatments for opioid dependence. Each blocks the human ether-a-go-go-related gene (hERG)-associated channel in vitro and represents a risk for QT prolongation. To compare the effects of 3 known hERG-associated channel
M Douglas Anglin et al.
The journal of behavioral health services & research, 36(2), 267-282 (2008-11-22)
Levo-alpha-acetylmethadol maintenance (LAAM) was compared to methadone maintenance (MM) on the behavioral performance of 315 heroin addicts before, during, and after 12 months of fully subsidized treatment. Assessments of drug use, criminal behavior, HIV risk behaviors, and employment and residential
Jan Gryczynski et al.
Substance abuse, 33(1), 30-39 (2012-01-24)
This study examined outcomes and their predictors among 181 probationers enrolling in opioid agonist maintenance with methadone or levo-alpha-acetylmethadol (LAAM). Participants were interviewed at treatment entry and 2-, 6-, and 12-month follow-ups. Treatment retention and frequency of heroin use, cocaine
No opiate substitutes for the masses of IDUs.
Jon Cohen
Science (New York, N.Y.), 329(5988), 165-167 (2010-07-10)
Lisa R Gerak et al.
Physiology & behavior, 93(1-2), 20-26 (2007-09-04)
Polydrug abuse remains a common problem among opioid abusers as well as patients in opioid maintenance programs. Although cocaine abuse has been reported in patients receiving methadone, the incidence of cocaine use in patients receiving l-alpha-acetylmethadol (LAAM) has not been

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