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Chemistry

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Also known as: 61-16-5, Methoxamine hcl, Methoxaminehydrochloride, 2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol hydrochloride, Mls000069686, 2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol;hydrochloride
Molecular Formula
C11H18ClNO3
Molecular Weight
247.72  g/mol
InChI Key
YGRFXPCHZBRUKP-UHFFFAOYSA-N

Methoxamine
An alpha-1 adrenergic agonist that causes prolonged peripheral VASOCONSTRICTION.
1 2D Structure

Methoxamine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol;hydrochloride
2.1.2 InChI
InChI=1S/C11H17NO3.ClH/c1-7(12)11(13)9-6-8(14-2)4-5-10(9)15-3;/h4-7,11,13H,12H2,1-3H3;1H
2.1.3 InChI Key
YGRFXPCHZBRUKP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C(C1=C(C=CC(=C1)OC)OC)O)N.Cl
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Hydrochloride, Methoxamine

2. Methoxamedrin

3. Methoxamine

4. Metoxamine Wellcome

5. Vasoxin

6. Vasoxine

7. Vasoxyl

8. Vasylox

9. Wellcome, Metoxamine

2.2.2 Depositor-Supplied Synonyms

1. 61-16-5

2. Methoxamine Hcl

3. Methoxaminehydrochloride

4. 2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol Hydrochloride

5. Mls000069686

6. 2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol;hydrochloride

7. Methoxamini Hydrochloridum

8. Nsc-757102

9. Ncgc00094108-02

10. Smr000058479

11. 2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol,hydrochloride

12. Methoxamine Hydrochloride (jan)

13. Sr-01000000198

14. Vasoxine Hcl

15. Prestwick_866

16. Vasoxyl (tn)

17. Methoxaminhydrochlorid

18. Vasoxine Hydrochloride

19. Methoxamine Hydrochlorid

20. Opera_id_389

21. Cas-61-16-5

22. Dsstox_cid_25782

23. Dsstox_rid_81124

24. Dsstox_gsid_45782

25. Mls001074122

26. Mls002222272

27. Schembl146117

28. Spectrum1500399

29. Chebi:6840

30. Chembl1201103

31. Hms1569l11

32. Hms1920n03

33. Pharmakon1600-01500399

34. Bcp19863

35. Tox21_111248

36. Tox21_500769

37. Ccg-38999

38. Nsc757102

39. Akos017343946

40. Lp00769

41. Ncgc00094108-01

42. Ncgc00094108-03

43. Ncgc00094108-04

44. Ncgc00094108-05

45. Ncgc00261454-01

46. Db-053802

47. Eu-0100769

48. Ft-0603257

49. Sw196992-3

50. D01020

51. M 6524

52. 058m607

53. A833069

54. Sr-01000000198-2

55. Sr-01000000198-6

56. Q26840987

57. Z2756841808

58. 2-amino-1-(2,5-dimethoxyphenyl)-propan-1-ol-hydrochlorid

59. 2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol;hydron;chloride

60. Alpha-(1-aminoethyl)-2,5-dimethoxybenzenemethanol Hydrochloride (1:1)

61. Methoxamine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

2.3 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 247.72 g/mol
Molecular Formula C11H18ClNO3
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass247.0975211 g/mol
Monoisotopic Mass247.0975211 g/mol
Topological Polar Surface Area64.7 Ų
Heavy Atom Count16
Formal Charge0
Complexity189
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Therapeutic Uses

Adrenergic alpha-Agonists; Sympathomimetics; Vasoconstrictor Agents

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


Methoxamine may be used intravenously in the treatment of hypotensive states or to relieve attacks of paroxysmal atrial tachycardia, particularly those associated with hypotension. /Methoxamine/

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


METHOXAMINE ... DOES NOT INCREASE VENTRICULAR RATE IN PATIENTS WITH HEART BLOCK. REFLEX BRADYCARDIA IS PROMINENT, &, THEREFORE, THE DRUG IS USED CLINICALLY TO RELIEVE ATTACKS OF PAROXYSMAL ATRIAL TACHYCARDIA. /METHOXAMINE/

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 166


THE DRUG IS USEFUL FOR THE TREATMENT OF HYPOTENSIVE STATES WHEN IT IS DESIRED TO RAISE BLOOD PRESSURE WITHOUT CARDIAC STIMULATION. HOWEVER, METHOXAMINE HAS VERY LITTLE EFFECT ON THE CAPACITANCE VEINS, SO THAT ITS USEFULNESS IS COMPROMISED, ESPECIALLY IN TREATMENT OF VARIOUS KINDS OF SHOCK.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 817


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


4.2 Drug Warning

Methoxamine should be used with caution in patients with hyperthyroidism, bradycardia, partial heart block, myocardial disease, or severe arteriosclerosis. Caution should be used to avoid overdosage of methoxamine, since it may cause undesirable hypertension and/or bradycardia.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 1999. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1999 (Plus Supplements)., p. 1129


Methoxamine can cause ventricular ectopic beats or severe bradycardia and decreased cardiac output. Decreased cardiac output may be especially harmful to geriatric patients and/or those with preexisting poor cerebral or coronary circulation. Bradycardia may be treated by administration of atropine. Methoxamine also increases cardiac work by increasing peripheral arterial resistance and may induce or exacerbate heart failure associated with a decreased myocardium. Some clinicians believe that the drug is contraindicated in shock caused by myocardial infarction. Large doses of methoxamine, especially if administered following repeated injections of the drug, may cause cardiac depression and a fall in blood pressure.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 1999. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1999 (Plus Supplements)., p. 1129


Methoxamine can cause severe peripheral and visceral vasoconstriction, reduced blood blow to vital organs, and decreased renal perfusion; reductions in glomerular filtration rate, urine output, and sodium excretion may occur as well as metabolic acidosis. These effects may be most likely to occur in hypovolemic patients. In addition, prolonged use of the drug may result in plasma volume depletion which may result in perpetuation of the shock state or the recurrence of hypotension when methoxamine is discontinued.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 1999. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1999 (Plus Supplements)., p. 1128


Methoxamine may cause restlessness, anxiety, nervousness, weakness, dizziness, precordial pain, tremor, respiratory distress, sweating, or pallor. Occasionally, injections of the drug may be followed by paresthesia in the extremities or feeling of coldness. A desire to void, a pilomotor response, and/or nausea and vomiting (often projectile) may also occur, especially with high doses. In addition, large doses of methoxamine may cause severe prolonged hypertension and severe headaches. Seizures and cerebral hemorrhage may result.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 1999. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1999 (Plus Supplements)., p. 1128


For more Drug Warnings (Complete) data for METHOXAMINE HYDROCHLORIDE (8 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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.)


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.)


5.2 Mechanism of Action

ITS PHARMACOLOGICAL PROPERTIES ARE ALMOST EXCLUSIVELY THOSE CHARACTERISTIC OF ALPHA-RECEPTOR STIMULATION, SINCE IT ACTS DIRECTLY AT THESE SITES. ... THE OUTSTANDING EFFECT IS AN INCREASE IN BLOOD PRESSURE DUE ENTIRELY TO VASOCONSTRICTION.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 165


METHOXAMINE, GIVEN INTRAVENOUSLY OR INTRAMUSCULARLY IN MAN, CAUSES A RISE IN SYSTOLIC & DIASTOLIC BLOOD PRESSURES THAT PERSISTS FOR 60 TO 90 MINUTES. THE PRESSOR EFFECT IS DUE ALMOST EXCLUSIVELY TO AN INCREASE IN PERIPHERAL RESISTANCE. CARDIAC OUTPUT IS DECREASED OR UNCHANGED. /METHOXAMINE/

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 165


METHOXAMINE HAS A RELATIVELY SELECTIVE ACTION ON POSTSYNAPTIC COMPARED WITH PRESYNAPTIC RECEPTOR OF PULMONARY ARTERY; BOTH SYSTEMS WERE OF SIMILAR SENSITIVITY TO NOREPINEPHRINE & EPINEPHRINE.

BEVAN JA; ON THE SUBCLASSIFICATION OF ALPHA-ADRENERGIC RECEPTORS; VASC NEUROEFF MECH, (PROC SYMP VASC NEUROEFF MECH); 251 (1980)


TRITIUM-LABELED METHOXAMINE CROSSED THE BLOOD-BRAIN BARRIER IN RAT. THUS METHOXAMINE IS CENTRALLY ACTIVE ALPHA-ADRENERGIC AGONIST & CONCEPT THAT HYPOTHALAMIC ADRENERGIC MECHANISMS ARE INVOLVED IN ELECTROENCEPHALOGIC & BEHAVIORAL AROUSAL IS SUPPORTED.

PICKWORTH ET AL; EXP NEUROL 57(3) 1011 (1977)


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