l-alpha-Noracetylmethadol

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 596844

CAS#: 38455-85-5

Description: l-alpha-Noracetylmethadol is discontinued (DEA controlled substance).


Chemical Structure

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l-alpha-Noracetylmethadol
CAS# 38455-85-5

Theoretical Analysis

MedKoo Cat#: 596844
Name: l-alpha-Noracetylmethadol
CAS#: 38455-85-5
Chemical Formula: C20H27NO
Exact Mass: 297.2093
Molecular Weight: 297.44
Elemental Analysis: C, 80.76; H, 9.15; N, 4.71; O, 5.38

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: l-alpha-Noracetylmethadol; alpha-Noracetylmethadol, l;

IUPAC/Chemical Name: 6-(methylamino)-4,4-diphenylheptan-3-ol

InChi Key: KYHAUJGXNUJCTC-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H27NO/c1-4-19(22)20(15-16(2)21-3,17-11-7-5-8-12-17)18-13-9-6-10-14-18/h5-14,16,19,21-22H,4,15H2,1-3H3

SMILES Code: OC(CC)C(C1=CC=CC=C1)(CC(NC)C)C2=CC=CC=C2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 297.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Newcombe DAL, Somogyi AA, Bochner F, White JM. Impaired psychomotor function and plasma methadone and levo-alpha-acetylmethadol (LAAM) concentrations in opioid-substitution patients. Exp Clin Psychopharmacol. 2017 Jun;25(3):223-233. doi: 10.1037/pha0000114. Epub 2017 Apr 17. PubMed PMID: 28414496.

2: Schrott LM, Sparber SB. Suppressed fever and hypersensitivity responses in chicks prenatally exposed to opiates. Brain Behav Immun. 2004 Nov;18(6):515-25. PubMed PMID: 15331122.

3: Deshmukh SV, Nanovskaya TN, Hankins GD, Ahmed MS. N-demethylation of levo-alpha-acetylmethadol by human placental aromatase. Biochem Pharmacol. 2004 Mar 1;67(5):885-92. PubMed PMID: 15104241.

4: Nanovskaya TN, Deshmukh SV, Miles R, Burmaster S, Ahmed MS. Transfer of L-alpha-acetylmethadol (LAAM) and L-alpha-acetyl-N-normethadol (norLAAM) by the perfused human placental lobule. J Pharmacol Exp Ther. 2003 Jul;306(1):205-12. Epub 2003 Apr 3. PubMed PMID: 12676878.

5: Kang J, Chen XL, Wang H, Rampe D. Interactions of the narcotic l-alpha-acetylmethadol with human cardiac K+ channels. Eur J Pharmacol. 2003 Jan 1;458(1-2):25-9. PubMed PMID: 12498903.

6: Huang W, Bemis PA, Slawson MH, Moody DE. Determination of l-alpha-acetylmethadol (LAAM), norLAAM, and dinorLAAM in clinical and in vitro samples using liquid chromatography with electrospray ionization and tandem mass spectrometry. J Pharm Sci. 2003 Jan;92(1):10-20. PubMed PMID: 12486677.

7: Schrott LM, Baumgart MI, Zhang X, Sparber SB. Prenatal opiate withdrawal activates the chick embryo hypothalamic pituitary-adrenal axis and dilates vitelline blood vessels via serotonin(2) receptors. J Pharmacol Exp Ther. 2002 Oct;303(1):257-64. PubMed PMID: 12235259.

8: Neff JA, Moody DE. Differential N-demethylation of l-alpha-acetylmethadol (LAAM) and norLAAM by cytochrome P450s 2B6, 2C18, and 3A4. Biochem Biophys Res Commun. 2001 Jun 15;284(3):751-6. PubMed PMID: 11396966.

9: Oda Y, Kharasch ED. Metabolism of levo-alpha-Acetylmethadol (LAAM) by human liver cytochrome P450: involvement of CYP3A4 characterized by atypical kinetics with two binding sites. J Pharmacol Exp Ther. 2001 Apr;297(1):410-22. PubMed PMID: 11259570.

10: O'Connor PG, Fiellin DA. Pharmacologic treatment of heroin-dependent patients. Ann Intern Med. 2000 Jul 4;133(1):40-54. Review. PubMed PMID: 10877739.

11: Moody DE, Alburges ME, Parker RJ, Collins JM, Strong JM. The involvement of cytochrome P450 3A4 in the N-demethylation of L-alpha-acetylmethadol (LAAM), norLAAM, and methadone. Drug Metab Dispos. 1997 Dec;25(12):1347-53. PubMed PMID: 9394023.

12: Vaupel DB, Jasinski DR. l-alpha-Acetylmethadol, l-alpha-acetyl-N-normethadol and l-alpha-acetyl-N,N-dinormethadol: comparisons with morphine and methadone in suppression of the opioid withdrawal syndrome in the dog. J Pharmacol Exp Ther. 1997 Nov;283(2):833-42. PubMed PMID: 9353405.

13: Wilkins DG, Valdez AS, Krueger GG, Rollins DE. Quantitative analysis of l-alpha-acetylmethadol, l-alpha-acetyl-N-normethadol, and l-alpha-acetyl-N,N-dinormethadol in human hair by positive ion chemical ionization mass spectrometry. J Anal Toxicol. 1997 Oct;21(6):420-6. PubMed PMID: 9323520.

14: Moody DE, Crouch DJ, Sakashita CO, Alburges ME, Minear K, Schulthies JE, Foltz RL. A gas chromatographic-positive ion chemical ionization-mass spectrometric method for the determination of I-alpha-acetylmethadol (LAAM), norLAAM, and dinorLAAM in plasma, urine, and tissue. J Anal Toxicol. 1995 Oct;19(6):343-51. PubMed PMID: 8926727.

15: Borzelleca JF, Egle JL Jr, Harris LS, Belleville JA. Toxicological evaluation of mu-agonists. Part II: Assessment of toxicity following 30 days of repeated oral dosing of male and female rats with levo-alpha-noracetylmethadol HCl (NorLAAM). J Appl Toxicol. 1995 Sep-Oct;15(5):339-55. PubMed PMID: 8666717.

16: Thomas BF, Jeffcoat AR, Myers MW, Mathews JM, Cook CE. Determination of l-alpha-acetylmethadol, l-alpha-noracetylmethadol and l-alpha-dinoracetylmethadol in plasma by gas chromatography-mass spectrometry. J Chromatogr B Biomed Appl. 1994 May 13;655(2):201-11. PubMed PMID: 8081466.

17: Verebey K, DePace A, Mulé SJ. Quantitation of l-alpha-acetylmethadol and its metabolites in human serum by capillary gas-liquid chromatography and nitrogen detection. J Chromatogr. 1985 Oct 11;343(2):339-48. PubMed PMID: 4066875.

18: Vernadakis A, Gibson A. Neurotoxicity of opiates during brain development: in vivo and in vitro studies. Prog Clin Biol Res. 1985;163C:245-53. PubMed PMID: 2986161.

19: James RC, Freeman RW, Harbison RD. L-alpha-acetylmethadol-induced tissue alterations in mice. Drug Chem Toxicol. 1984;7(1):91-112. PubMed PMID: 6723548.

20: Roerig DL, Dahl RR, Dawson CA, Wang RI. Uptake of l-alpha-acetylmethadol (LAAM) and its analgesically active metabolites, nor-LAAM and dinor-LAAM, in the isolated perfused rat lung. Drug Metab Dispos. 1983 Sep-Oct;11(5):411-6. PubMed PMID: 6138224.