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Chemistry

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Also known as: Levacetylmethadol, Laam, Levo-alphacetylmethadol, Levomethadyl, Orlaam, 1-alpha-acetylmethadol

Molecular Formula

C₂₃H₃₁NO₂

Molecular Weight

353.5 g/mol

InChI Key

XBMIVRRWGCYBTQ-AVRDEDQJSA-N

FDA UNII

R3B637Y991

A narcotic analgesic with a long onset and duration of action.

1 2D Structure

Levomethadyl Acetate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 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

2.1.3 InChI Key

XBMIVRRWGCYBTQ-AVRDEDQJSA-N

2.1.4 Canonical SMILES

CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C

2.1.5 Isomeric SMILES

CC[C@@H](C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C

2.2 Other Identifiers

2.2.1 UNII

R3B637Y991

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (3r,6r)-3-acetoxy-6-dimethylamino-4,4-diphenylheptane

2. 6-(dimethylamino)-4,4-diphenyl-3-heptanol Acetate

3. Acemethadone

4. Acetylmethadol

5. Alphacetylmethadol

6. Amidolacetate

7. Dimepheptanol

8. Laam

9. Levo Alpha Acetylmethadol

10. Levo-alpha-acetylmethadol

11. Levoacetylmethadol

12. Levomethadyl

13. Levomethadyl Acetate Hydrochloride

14. Methadol

15. Methadyl Acetate

16. Orlaam

2.3.2 Depositor-Supplied Synonyms

1. Levacetylmethadol

2. Laam

3. Levo-alphacetylmethadol

4. Levomethadyl

5. Orlaam

6. 1-alpha-acetylmethadol

7. Levo-methadyl Acetate

8. 1477-40-3

9. (-)-alpha-acetylmethadol

10. Levo-alpha-acetylmethadol

11. Levacetilmetadol

12. Alpha-l-acetylmethadol

13. Levacetylmethadolum

14. Levacetylmethadol [inn]

15. Alpha-(-)-acetylmethadol

16. Levacetilmetadol [inn-spanish]

17. Levacetylmethadolum [inn-latin]

18. L-alpha-acetylmethadol

19. Levoacetyl Methadol

20. Levomethadyl Acetate [usan]

21. Dea No. 9648

22. (-)-6-(dimethylamino)-4,4-diphenyl-3-heptanol Acetate (ester)

23. Laa-m

24. Levacetylmethadol (inn)

25. 34433-66-4

26. Levomethadyl Acetate (usan)

27. Chebi:6441

28. (1s,4s)-4-(dimethylamino)-1-ethyl-2,2-diphenylpentyl Acetate

29. [(3s,6s)-6-(dimethylamino)-4,4-diphenylheptan-3-yl] Acetate

30. R3b637y991

31. N-alpha-acetylmethadol

32. (3s,6s)-6-(dimethylamino)-4,4-diphenylheptan-3-yl Acetate

33. Benzeneethanol, Beta-((2s)-2-(dimethylamino)propyl)-alpha-ethyl-beta-phenyl-, Acetate (ester), (alphas)-

34. Benzeneethanol, Beta-(2-(dimethylamino)propyl)-alpha-ethyl-beta-phenyl-, Acetate (ester), (s-(r*,r*))-

35. Unii-r3b637y991

36. 3-heptanol, 6-(dimethylamino)-4,4-diphenyl-, Acetate (ester), (3s,6s)-(-)-

37. Benzeneethanol, Beta-[(2s)-2-(dimethylamino)propyl]-alpha-ethyl-beta-phenyl-, Acetate (ester), (alphas)-

38. Benzeneethanol, Beta-[2-(dimethylamino)propyl]-alpha-ethyl-beta-phenyl-, Acetate (ester), [s-(r*,r*)]-

39. Chembl1514

40. Bidd:pxr0155

41. Schembl93805

42. Bidd:gt0373

43. Gtpl7212

44. Dtxsid3023211

45. Levacetylmethadol [mart.]

46. Levomethadyl Acetate [mi]

47. (3s,6s)-6-(dimethylamino)-4,4-diphenylheptan-2-yl Acetate

48. Levacetylmethadol [who-dd]

49. Zinc1530967

50. Levacetylmethadol [ema Epar]

51. Db01227

52. Benzeneethanol, Beta-(2-(dimethylamino)propyl)-alpha-ethyl-beta-phenyl-, Acetate(ester), (-)

53. Ncgc00247347-01

54. [s-(r*,r*)]-beta-[2-dimethylamino)propyl]-alpha-ethyl-beta-phenylbenzeneethanol Acetate (ester)

55. Ft-0700555

56. C08012

57. D04716

58. Q411799

59. (1s,4s)-(6-dimethylamino-4,4-diphenyl-heptan-3-yl) Acetate

60. 3-heptanol, 6-(dimethylamino)-4,4-diphenyl-, Acetate (ester), (3s,6s)-(-)- (8ci)

61. Benzeneethanol, .beta.-(2-(dimethylamino)propyl)-.alpha.-ethyl-.beta.-phenyl-, Acetate (ester), (-)-

62. Benzeneethanol, Beta-[(2s)-2-(dimethylamino)propyl]-alpha-ethyl-beta-phenyl-, Acetate (ester), (alphas)- (9ci)

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₃₁NO₂
Molecular Weight	353.5 g/mol
XLogP3	4.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	9
Exact Mass	353.235479232 g/mol
Monoisotopic Mass	353.235479232 g/mol
Topological Polar Surface Area	29.5 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	404
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment and management of opiate dependence. It is sometimes used to treat severe pain in terminal patients.

ORLAAM is indicated for the substitution maintenance treatment of opiate addiction in adults previously treated with methadone, as part of a comprehensive treatment plan including medical, social and psychological care.

ORLAAM should be administered under the supervision of physicians with experience in addiction treatment and whenever practicable, in centres specialising in the treatment of drug addiction.

ORLAAM is not intended for take home use.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Levomethadyl acetate (also known as LAAM) is a synthetic synthetic opioid analgesic with multiple actions quantitatively similar to those as morphine, the most prominent of which involve the central nervous system and organs composed of smooth muscle. However, levomethadyl acetate is more active and more toxic than morphine. The principal actions of therapeutic value are analgesia and sedation and detoxification or temporary maintenance in narcotic addiction. In this respect, the drug is similar to Methadone and also has structural similarities to it. The levomethadyl acetate abstinence syndrome, although qualitatively similar to that of morphine, differs in that the onset is slower, the course is more prolonged, and the symptoms are less severe.

5.2 MeSH Pharmacological Classification

Analgesics, Opioid

Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)

5.3 ATC Code

N02AC

N - Nervous system

N07 - Other nervous system drugs

N07B - Drugs used in addictive disorders

N07BC - Drugs used in opioid dependence

N07BC03 - Levacetylmethadol

5.4 Absorption, Distribution and Excretion

Absorption

Levomethadyl acetate is rapidly absorbed from an oral solution.

5.5 Metabolism/Metabolites

Levomethadyl acetate is demethylated to nor-levomethadyl acetate which is again demethylated to dinor-levomethadyl acetate. This extensive first pass metabolism produces 2 metabolites that are more active than the parent drug.

5.6 Biological Half-Life

2.6 days

5.7 Mechanism of Action

Opiate receptors (Mu, Kappa, Delta) are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Levomethadyl acetate effectively opens calcium-dependent inwardly rectifying potassium channels (OP1 receptor agonist), resulting in hyperpolarization and reduced neuronal excitability.

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