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CAS 156-34-3

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CHEMISTRY

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1 Intermediates

1 Intermediates

Chemistry

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Also known as: L-amphetamine, Levamphetamine, (r)-amphetamine, 156-34-3, (2r)-1-phenylpropan-2-amine, (-)-amphetamine

Molecular Formula

C₉H₁₃N

Molecular Weight

135.21 g/mol

InChI Key

KWTSXDURSIMDCE-MRVPVSSYSA-N

FDA UNII

R87US8P740

A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.

1 2D Structure

CAS 156-34-3

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-1-phenylpropan-2-amine

2.1.2 InChI

InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1

2.1.3 InChI Key

KWTSXDURSIMDCE-MRVPVSSYSA-N

2.1.4 Canonical SMILES

CC(CC1=CC=CC=C1)N

2.1.5 Isomeric SMILES

C[C@H](CC1=CC=CC=C1)N

2.2 Other Identifiers

2.2.1 UNII

R87US8P740

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Amfetamine

2. Amphetamine

3. Amphetamine Sulfate

4. Amphetamine Sulfate (2:1)

5. Centramina

6. Desoxynorephedrin

7. Fenamine

8. L Amphetamine

9. L-amphetamine

10. Levo Amphetamine

11. Levo-amphetamine

12. Levoamphetamine

13. Mydrial

14. Phenamine

15. Phenopromin

16. Sulfate, Amphetamine

17. Thyramine

2.3.2 Depositor-Supplied Synonyms

1. L-amphetamine

2. Levamphetamine

3. (r)-amphetamine

4. 156-34-3

5. (2r)-1-phenylpropan-2-amine

6. (-)-amphetamine

7. (r)-1-phenylpropan-2-amine

8. L-(r)-amphetamine

9. (r)-alpha-methylbenzeneethanamine

10. (r)-alpha-methylphenethylamine

11. (-)-phenylisopropylamine

12. L-alpha-methylphenethylamine

13. Amphetamine L-form

14. Amfetamine, (r)-

15. Levamfetamine (in Methanol)

16. Chembl19393

17. Chebi:42724

18. R87us8p740

19. Levamphetaminum

20. Levamfetamina [dcit]

21. Levamfetamina

22. Levamfetaminum

23. Levanfetamina

24. R-amphetamine

25. Levamfetamine [inn:ban]

26. R(-)amphetamine

27. Levamfetaminum [inn-latin]

28. Levanfetamina [inn-spanish]

29. (-)-alpha-methylphenethylamine

30. Einecs 205-850-8

31. L-amphetamine Hydrochloride

32. Unii-r87us8p740

33. (r)-phenaminum

34. Phenethylamine, Alpha-methyl-, (-)-

35. Benzeneethanamine, Alpha-methyl-, (r)-

36. L-a-methylphenethylamine

37. (r)-phenylisopropylamine

38. (r)-a-methylphenethylamine

39. Levamfetamine [inn]

40. Schembl2636

41. (r)-a-methylbenzeneethanamine

42. (r)-a-methyl-benzeneethanamine

43. Gtpl2146

44. (r)-amphetamine; Levamphetamine

45. Amphetamine L-form [mi]

46. Dtxsid20166016

47. (r)-alpha-methyl-benzeneethanamine

48. Act09042

49. Zinc6036847

50. Bdbm50022721

51. Pdsp1_001510

52. Pdsp2_001494

53. Akos022172419

54. C105

55. (r)-1-methyl-2-phenyl-ethylamine

56. (-)-(r)-.alpha.-methylphenethylamine

57. (-)-(r)-.alpha.-methylbenzeneethanamine

58. Q2506823

59. R(-)-amphetamine (levo-amphetamine), 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₃N
Molecular Weight	135.21 g/mol
XLogP3	1.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	2
Exact Mass	135.104799419 g/mol
Monoisotopic Mass	135.104799419 g/mol
Topological Polar Surface Area	26 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	84.7
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Central Nervous System Stimulants

A loosely defined group of drugs that tend to increase behavioral alertness, agitation, or excitation. They work by a variety of mechanisms, but usually not by direct excitation of neurons. The many drugs that have such actions as side effects to their main therapeutic use are not included here. (See all compounds classified as Central Nervous System Stimulants.)

Adrenergic Agents

Drugs that act on adrenergic receptors or affect the life cycle of adrenergic transmitters. Included here are adrenergic agonists and antagonists and agents that affect the synthesis, storage, uptake, metabolism, or release of adrenergic transmitters. (See all compounds classified as Adrenergic Agents.)

Adrenergic Uptake Inhibitors

Drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants (ANTIDEPRESSIVE AGENTS, TRICYCLIC) and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin. (See all compounds classified as Adrenergic Uptake Inhibitors.)

Dopamine Agents

Any drugs that are used for their effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons. (See all compounds classified as Dopamine Agents.)

Dopamine Uptake Inhibitors

Drugs that block the transport of DOPAMINE into axon terminals or into storage vesicles within terminals. Most of the ADRENERGIC UPTAKE INHIBITORS also inhibit dopamine uptake. (See all compounds classified as Dopamine Uptake Inhibitors.)

Sympathomimetics

Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. (See all compounds classified as Sympathomimetics.)

4.2 Metabolism/Metabolites

Amphetamine has known human metabolites that include 4-Hydroxyamphetamine.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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