Levacetylmethadol

Levacetylmethadol
Clinical data
Trade names	OrLAAM
Routes of; administration	By mouth
ATC code	N07BC03 (WHO) ;
Legal status
Legal status	AU: S8 (Controlled drug); CA: Schedule I; DE: Anlage III (Special prescription form required); US: Schedule II;
Pharmacokinetic data
Protein binding	~80%
Metabolism	CYP3A4
Elimination half-life	2.6 days
Identifiers
	IUPAC name (3S,6S)-(6-dimethylamino-4,4-diphenyl-heptan-3-yl) acetate;
CAS Number	1477-40-3 ; 43033-72-3 (hydrochloride);
PubChem CID	15130;
IUPHAR/BPS	7212;
DrugBank	DB01227 ;
ChemSpider	14401 ;
UNII	R3B637Y991;
KEGG	D04716 ;
ChEMBL	ChEMBL1514 ;
CompTox Dashboard (EPA)	DTXSID3023211 ;
Chemical and physical data
Formula	C23H31NO2
Molar mass	353.506 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC[C@@H](C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C;
	InChI InChI=1S/C23H31NO2/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/t18-,22-/m0/s1 ; Key:XBMIVRRWGCYBTQ-AVRDEDQJSA-N ;
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Levacetylmethadol (INN), levomethadyl acetate (USAN), OrLAAM (trade name) or levo-α-acetylmethadol (LAAM)^[1]^[2] is a synthetic opioid similar in structure to methadone. It has a long duration of action due to its active metabolites.

^ US 3021360, Pholand A, "3-Acetoxy-4,4-diphenyl-6-methylaminoheptane", issued 12 February 1962, assigned to Eli Lilly and Company
^ US 2565592, Clark RL, "Alpha-d1-4-acetoxy-1-methyl-3,3-diphenylhexylamine and salts", issued 28 August 1951, assigned to Merck & Company

[1] US 3021360, Pholand A, "3-Acetoxy-4,4-diphenyl-6-methylaminoheptane", issued 12 February 1962, assigned to Eli Lilly and Company

[2] US 2565592, Clark RL, "Alpha-d1-4-acetoxy-1-methyl-3,3-diphenylhexylamine and salts", issued 28 August 1951, assigned to Merck & Company

[1]

[2]

Clinical data


Trade names	OrLAAM
Routes of administration	By mouth
ATC code	N07BC03 (WHO)
Legal status
Legal status	AU: S8 (Controlled drug) CA: Schedule I DE: Anlage III (Special prescription form required) US: Schedule II
Pharmacokinetic data
Protein binding	~80%
Metabolism	CYP3A4
Elimination half-life	2.6 days
Identifiers
IUPAC name (3S,6S)-(6-dimethylamino-4,4-diphenyl-heptan-3-yl) acetate
CAS Number	1477-40-3^Y 43033-72-3 (hydrochloride)
PubChem CID	15130
IUPHAR/BPS	7212
DrugBank	DB01227^N
ChemSpider	14401^N
UNII	R3B637Y991
KEGG	D04716^Y
ChEMBL	ChEMBL1514^N
CompTox Dashboard (EPA)	DTXSID3023211
Chemical and physical data
Formula	C₂₃H₃₁NO₂
Molar mass	353.506 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC[C@@H](C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C
InChI InChI=1S/C23H31NO2/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/t18-,22-/m0/s1^N Key:XBMIVRRWGCYBTQ-AVRDEDQJSA-N^N
^NY (what is this?) (verify)