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Chemistry

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Also known as: Mephenterdrine, Mefenterdrin, Mephenterdrinum, Mephetedrine, Mefentermin, Vialin

Molecular Formula

C₁₁H₁₇N

Molecular Weight

163.26 g/mol

InChI Key

RXQCGGRTAILOIN-UHFFFAOYSA-N

FDA UNII

TEZ91L71V4

A sympathomimetic agent with specificity for alpha-1 adrenergic receptors. It is used to maintain BLOOD PRESSURE in hypotensive states such as following SPINAL ANESTHESIA.

1 2D Structure

Mephentermine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N,2-dimethyl-1-phenylpropan-2-amine

2.1.2 InChI

InChI=1S/C11H17N/c1-11(2,12-3)9-10-7-5-4-6-8-10/h4-8,12H,9H2,1-3H3

2.1.3 InChI Key

RXQCGGRTAILOIN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)(CC1=CC=CC=C1)NC

2.2 Other Identifiers

2.2.1 UNII

TEZ91L71V4

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Mephentermine Sulfate

2. Mephentermine Sulfate (2:1)

3. Sulfate, Mephentermine

2.3.2 Depositor-Supplied Synonyms

1. Mephenterdrine

2. Mefenterdrin

3. Mephenterdrinum

4. Mephetedrine

5. Mefentermin

6. Vialin

7. N-methylphentermine

8. 100-92-5

9. Wyfentermina

10. Mephine

11. Wyamine

12. N,2-dimethyl-1-phenylpropan-2-amine

13. Mephentermine Sulfate

14. Wy-585

15. 2-methyl-2-methylamino-1-phenylpropane

16. 2-methylamino-2-methyl-1-phenylpropane

17. Mephentermine (inn)

18. N-methyl-omega-phenyl-tert-butylamine

19. Chebi:6755

20. Tez91l71v4

21. Benzeneethanamine, N,.alpha.,.alpha.-trimethyl-

22. Mefentermina

23. Mephenterminum

24. N,.alpha.,.alpha.-trimethylphenethylamine

25. Methyl(2-methyl-1-phenylpropan-2-yl)amine

26. Mephentermine Sodium

27. Phenethylamine, N,.alpha.,.alpha.-trimethyl-

28. Mephentermine [inn]

29. Mephentermine [inn:ban]

30. Mefentermina [inn-spanish]

31. Mephenterminum [inn-latin]

32. N,2-dimethyl-1-phenylpropan-2-amine;n,2-dimethyl-1-phenylpropan-2-amine

33. N-methyl-omega-phenyl-t-butylamine

34. Omega-phenyl-tert-butyl-methylamine

35. N,alpha,alpha-trimethylphenethylamine

36. N,alpha,alpha-trimethylbenzeneethanamine

37. Hsdb 2172

38. Benzeneethanamine, N,alpha,alpha-trimethyl-

39. Ncgc00016570-01

40. Einecs 202-901-6

41. Cas-1212-72-2

42. Brn 1363850

43. Unii-tez91l71v4

44. Phenethylamine, N,alpha,alpha-trimethyl-

45. Fentermin (salt/mix)

46. (1,1-dimethyl-2-phenylethyl)methylamine

47. Spectrum_001611

48. Prestwick0_000726

49. Prestwick1_000726

50. Prestwick2_000726

51. Prestwick3_000726

52. Spectrum2_000474

53. Spectrum3_001220

54. Spectrum4_000188

55. Spectrum5_001008

56. Mephentermine [mi]

57. Mephentermine [hsdb]

58. Bspbio_000652

59. Bspbio_002640

60. Kbiogr_000735

61. Kbioss_002091

62. Mephentermine [vandf]

63. Divk1c_000229

64. Schembl121178

65. Spbio_000608

66. Spbio_002591

67. Mephentermine [who-dd]

68. Bpbio1_000718

69. Gtpl7222

70. Chembl1201234

71. Dtxsid4023256

72. Bdbm81455

73. Kbio1_000229

74. Kbio2_002091

75. Kbio2_004659

76. Kbio2_007227

77. Kbio3_002140

78. Ninds_000229

79. Cas_3677

80. Nsc_3677

81. Zinc8132748

82. .omega.-phenyl-tert-butyl-methylamine

83. N-methyl-.omega.-phenyl-t-butylamine

84. Akos006281398

85. Db01365

86. Idi1_000229

87. N,2-dimethyl-1-phenyl-2-propanamine #

88. N-methyl-.omega.-phenyl-tert-butylamine

89. Ncgc00016570-02

90. Ncgc00016570-03

91. Sbi-0051802.p002

92. Ab00053662

93. N,.alpha.,.alpha.-trimethylbenzeneethanamine

94. C07889

95. D08180

96. Ab00053662_08

97. 100m925

98. N,.alpha.,.alpha.-trimethyl-.beta.-phenethylamine

99. Q6817800

100. Brd-k18194590-065-05-6

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₇N
Molecular Weight	163.26 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	3
Exact Mass	163.136099547 g/mol
Monoisotopic Mass	163.136099547 g/mol
Topological Polar Surface Area	12 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	123
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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 Therapeutic Uses

Adrenergic alpha-Agonists; Adrenergic Agents; Sympathomimetics; Vasoconstrictor Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

Mephentermine ... is used to prevent hypotension, which frequently accompanies spinal anesthesia.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 217

IT IS NOT RECOMMENDED FOR ROUTINE USE IN MANAGEMENT OF SHOCK, ESPECIALLY HYPOVOLEMIC SHOCK, ALTHOUGH IT CAN BE GIVEN AS INTERIM DRUG WHILE PREPARATIONS ARE BEING MADE FOR FLUID REPLACEMENT & OTHER MEASURES. /SULFATE/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 169

...FREE BASE CAN BE EMPLOYED TOPICALLY AS MYDRIATIC.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 816

For more Therapeutic Uses (Complete) data for MEPHENTERMINE (9 total), please visit the HSDB record page.

4.2 Drug Warning

Mephentermine may produce arrhythmias, including extrasystoles, and AV block and hypertension. Arrhythmias are most likely to occur in patients with heart disease or those receiving other drugs which may increase cardiac irritability such as cyclopropane or halogenated hydrocarbon general anesthetics. /Mephentermine sulfate/

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 888

The CNS stimulating effects of mephentermine may result in nervousness, anxiety, seizures, or tachycardia. Large overdosage of the drug has caused visual hallucinations of colored geometric forms, paranoid psychosis, and euphoria. Drowsiness, weeping, incoherence, weakness, numbness, and tingling of the extremities have been reported. Withdrawal of the drug results in rapid disappearance of adverse CNS effects. /Mephentermine sulfate/

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 888

AS THE FREE BASE IS CURRENTLY USED, UNTOWARD EFFECTS ARE VERY UNCOMMON.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 816

MEPHENTERMINE MAY INCR UTERINE CONTRACTIONS ESPECIALLY DURING THE THIRD TRIMESTER OF PREGNANCY &, THEREFORE, SHOULD NOT BE USED IN PREGNANT WOMEN UNLESS THE POTENTIAL BENEFITS OUTWEIGH THE POSSIBLE RISKS. /MEPHENTERMINE SULFATE/

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 889

For more Drug Warnings (Complete) data for MEPHENTERMINE (10 total), please visit the HSDB record page.

4.3 Drug Indication

Used to maintain blood pressure in hypotensive states.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Mephentermine is a sympathomimetic agent with mainly indirect effects on adrenergic receptors. It is used to maintain blood pressure in hypotensive states, for example, following spinal anesthesia. Although the central stimulant effects of mephentermine are much less than those of amphetamine, its use may lead to amphetamine-type dependence. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1248)

5.2 MeSH Pharmacological Classification

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.)

Vasoconstrictor Agents

Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)

Adrenergic alpha-1 Receptor Agonists

Compounds that bind to and activate ADRENERGIC ALPHA-1 RECEPTORS. (See all compounds classified as Adrenergic alpha-1 Receptor Agonists.)

5.3 ATC Code

C - Cardiovascular system

C01 - Cardiac therapy

C01C - Cardiac stimulants excl. cardiac glycosides

C01CA - Adrenergic and dopaminergic agents

C01CA11 - Mephentermine

5.4 Absorption, Distribution and Excretion

...MEPHENTERMINE.../IS/ WELL ABSORBED FROM DIGESTIVE TRACT. .../IT/ MAY BE ABSORBED TO A GREATER OR LESSER EXTENT FROM NASAL MUCOSA.

Thienes, C., and T.J. Haley. Clinical Toxicology. 5th ed. Philadelphia: Lea and Febiger, 1972., p. 108

THE MAJORITY OF THE DRUG IS EXCRETED IN THE URINE WITHIN 24 HR. MEPHENTERMINE IS REABSORBED IN THE RENAL TUBULES. EXCRETION OF THE DRUG & ITS METABOLITES IS MORE RAPID IN ACIDIC URINE.

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 888

5.5 Metabolism/Metabolites

Hepatic, by N-demethylation and then p-hydroxylation.

MEPHENTERMINE IS METABOLIZED IN THE LIVER BY N-DEMETHYLATION & SUBSEQUENT P-HYDROXYLATION TO NORMEPHENTERMINE & P-HYDROXYNORMEPHENTERMINE. /SULFATE/

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 888

MEPHENTERMINE WAS METABOLIZED IN VITRO BY RABBIT LIVER MICROSOMES TO PHENTERMINE (II), N-HYDROXYMEPHENTERMINE (III), & N-HYDROXYPHENTERMINE. METABOLITES (II) & (III) PLUS UNCHANGED MEPHENTERMINE FOUND IN URINE OF HUMAN ADMIN SINGLE DOSE OF MEPHENTERMINE SULFATE.

PMID:2665 BECKETT AH, BELANGER PM; J PHARM PHARMACOL 27 (12): 928 (1975)

Metabolites of mephentermine (MP), phentermine (Ph), p-hydroxy-MP, p-hydroxy-Ph, N-hydroxy-MP and N-hydroxy-Ph on incubation with rat liver microsomal and cytosolic preparations were identified by glc and glc mass spectrometry. Identification of the metabolites indicated the following new metabolic routes of MP: NADPH dependent microsomal formation of p-hydroxy-MP from MP, of p-hydroxy-Ph from p-hydroxy-MP, and the NADH-dependent microsomal formation of Ph from N-hydroxy-Ph.

PMID:1523866 Mori MA, et al; Xenobiotica 22 (4):451-7 (1992)

The urinary excretion of mephentermine (I) and its major metabolite phentermine (II) in human volunteers over a period of several days after oral admin of the drug is described. The total proportion of the drug excreted during 54 hr was 57 to 83%. The ingestion of acetazolamide shortly after admin of I resulted in decr in excretion of both I and II during one day. The administration of furosemide only produced a urinary diluting effect during 2-4 hr after admin.

PMID:16867696 Delbeke FT, Debackers M; J Pharm Biomed Anal 3 (2): 141-8 (1985)

5.6 Biological Half-Life

17 to 18 hours.

17 to 18 hours

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 2743

5.7 Mechanism of Action

Mephentermine is an alpha adrenergic receptor agonist, but also acts indirectly by releasing endogenous norepinephrine. Cardiac output and systolic and diastolic pressures are usually increased. A change in heart rate is variable, depending on the degree of vagal tone. Sometimes the net vascular effect may be vasodilation. Large doses may depress the myocardium or produce central nervous system (CNS) effects.

Mephentermine is a sympathomimetic drug that acts both directly and indirectly; it has many similarities to ephedrine. After an intramuscular injection, the onset of action is prompt (within 5 to 15 minutes), and effects may last for several hours.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 216

Since the drug releases norepinephrine, cardiac contraction is enhanced and cardiac output and systolic and diastolic pressures are usually increased. The change in heart rate is variable, depending on the degree of vagal tone.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 216

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