Metaraminol Bitartrate
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MedKoo CAT#: 318195

CAS#: 33402-03-8 (tartrate)

Description: Metaraminol bitartrate is a sympathomimetic agent that acts predominantly at alpha-1 adrenergic receptors. It has been used primarily as a vasoconstrictor in the treatment of hypotension.

Chemical Structure

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Metaraminol Bitartrate
CAS# 33402-03-8 (tartrate)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318195
Name: Metaraminol Bitartrate
CAS#: 33402-03-8 (tartrate)
Chemical Formula: C13H19NO8
Exact Mass: 0.00
Molecular Weight: 317.290
Elemental Analysis: C, 49.21; H, 6.04; N, 4.41; O, 40.34

Price and Availability

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1g USD 150 Ready to ship
2g USD 250 Ready to ship
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Related CAS #: 33402-03-8 (tartrate)   54-49-9 (free base)   5967-52-2 (HCl)   5967-53-3 (oxalate dihydrate)  

Synonym: Metaraminol Bitartrate; Metaraminol (tartrate); Araminum; UNII-ZC4202M9P3; Levicor; Metaraminol Tartrate; Tartrate, Metaraminol; Araminol; Bitartrate, Metaraminol;

IUPAC/Chemical Name: 3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol;(2R,3R)-2,3-dihydroxybutanedioic acid

InChi Key: VENXSELNXQXCNT-YDYUUSCQSA-N

InChi Code: InChI=1S/C9H13NO2.C4H6O6/c1-6(10)9(12)7-3-2-4-8(11)5-7;5-1(3(7)8)2(6)4(9)10/h2-6,9,11-12H,10H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t6-,9-;/m0./s1

SMILES Code: CC(C(C1=CC(=CC=C1)O)O)N.C(C(C(=O)O)O)(C(=O)O)O

Appearance: White to off-white crystalline powder.

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Metaraminol is an adrenergic agonist that acts predominantly at alpha adrenergic receptors and also stimulates the release of norepinephrine.
In vitro activity: The ability of a-methyl amino-acids and their corresponding amines to restore the sympathomimetic actions of tyramine, and the uptake of the aminoacids and the amines, were studied in isolated tissue preparations obtained from reserpine pretreated animals. Lower concentrations of metaraminol restored the responses to tyramine (Fig. 1) while higher concentrations (10,fg/ml and 30 jug/ml for 30 min; nine trials) failed to restore the responses to the same doses of tyramine. This appeared surprising and,therefore, the influence of metaraminol in modifying the responses to tyramine and noradrenaline was studied in nine preparations obtained from normal rats. Higher concentrations of metaraminol completely blocked the relaxant effect of tyramine but the response to noradrenaline was not affected. Lower concentration of metaraminol, however, failed to modify responses to tyramine or noradrenaline. It is important to note (Fig. 2) that following metaraminol and a-methylnoradrenaline responses to the lowest dose of tyramine were not only restored but were highly potentiated and the restored responses were now significantly (P<0 05) greater than normal responses. Metaraminol could restore the responses to tyramine of isolated rat ileum, perfused rabbit ear and heart preparations. Thus, like noradrenaline, metaraminol too can be taken up and released by tissues of reserpine treated animals. Reference Br J Pharmacol. 1970 Dec;40(4):689-701. https://pubmed.ncbi.nlm.nih.gov/5495174/
In vivo activity: Rats were placed at 270 C or 40 C and given metaraminol ((10 mg/kg)/day) in their drinking water for 8 weeks. One experiment was run using adrenal demedullated rats. These animals were treated with metaraminol, as mentioned above, and kept at 40 C for 4 weeks. Body temperature and metabolic rate were determined at selected intervals. Urine was collected on day 7 of each week and analysed for adrenaline, noradrenaline, metanephrine, normetanephrine and 3-methoxy-4-hydroxyphenylglycol (MHPG). All animals survived the metaraminol treatment and no change in metabolic rate or body temperature was seen. Metaraminol depressed the growth rate of the rats. Metaraminol caused a fall in tissue noradrenaline concentrations, with only negligible quantities being found in brain, heart, lung, liver, kidney and spleen. The increase in MHPG excretion, seen during metaraminol treatment, suggests an increased rate of noradrenaline turnover. Daily metaraminol treatment for several weeks increased the catecholamine content of the intact adrenals and the adrenaline levels of the previously demedullated adrenal glands. In the present study, chronic daily treatment with metaraminol resulted in high tissue levels of the drug and virtual depletion of noradrenaline. Reference: Br J Pharmacol. 1970 Nov;40(3):418-25. https://pubmed.ncbi.nlm.nih.gov/5497793/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 0.0 0.00

Preparing Stock Solutions

The following data is based on the product molecular weight 317.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Alabaster VA, Bakhle YS. The removal of noradrenaline in the pulmonary circulation of rat isolated lungs. Br J Pharmacol. 1973 Feb;47(2):325-31. doi: 10.1111/j.1476-5381.1973.tb08330.x. PMID: 4722046; PMCID: PMC1776564. 2. Gulati OD, Parikh HM, Ringe SY, Sherlekar ML. An investigation of alpha-methyl amino-acids and their derivatives on isolated tissue preparations. Br J Pharmacol. 1970 Dec;40(4):689-701. doi: 10.1111/j.1476-5381.1970.tb10647.x. PMID: 5495174; PMCID: PMC1702915. 3. Iwabuchi Y, Aoki C, Masuhara T. Effects of metaraminol on the secretion of fluid and glycoproteins from the rat submandibular gland. Jpn J Pharmacol. 1989 Apr;49(4):491-500. doi: 10.1254/jjp.49.491. PMID: 2724688. 4. Johnson GE, Pugsley TA. Effects of chronic metaraminol treatment on the sympathetic activity of intact and adrenal demedullated rats kept in warm or cold environments. Br J Pharmacol. 1970 Nov;40(3):418-25. doi: 10.1111/j.1476-5381.1970.tb10623.x. PMID: 5497793; PMCID: PMC1703157.
In vitro protocol: 1. Alabaster VA, Bakhle YS. The removal of noradrenaline in the pulmonary circulation of rat isolated lungs. Br J Pharmacol. 1973 Feb;47(2):325-31. doi: 10.1111/j.1476-5381.1973.tb08330.x. PMID: 4722046; PMCID: PMC1776564. 2. Gulati OD, Parikh HM, Ringe SY, Sherlekar ML. An investigation of alpha-methyl amino-acids and their derivatives on isolated tissue preparations. Br J Pharmacol. 1970 Dec;40(4):689-701. doi: 10.1111/j.1476-5381.1970.tb10647.x. PMID: 5495174; PMCID: PMC1702915.
In vivo protocol: 1. Iwabuchi Y, Aoki C, Masuhara T. Effects of metaraminol on the secretion of fluid and glycoproteins from the rat submandibular gland. Jpn J Pharmacol. 1989 Apr;49(4):491-500. doi: 10.1254/jjp.49.491. PMID: 2724688. 2. Johnson GE, Pugsley TA. Effects of chronic metaraminol treatment on the sympathetic activity of intact and adrenal demedullated rats kept in warm or cold environments. Br J Pharmacol. 1970 Nov;40(3):418-25. doi: 10.1111/j.1476-5381.1970.tb10623.x. PMID: 5497793; PMCID: PMC1703157

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1: Koga S, Shiraishi K, Saito Y. Post-traumatic priapism treated with metaraminol
bitartrate: case report. J Trauma. 1990 Dec;30(12):1591-3. PubMed PMID: 2258979.

2: GRIVAUX M. [Metaraminol bitartrate in the treatment of shock]. Sem Hop. 1963
May 26;39:1314-9. French. PubMed PMID: 13950601.

3: MEIJLER FL, MEERSCHWAM IS, KOSTER M. [The influence of metaraminol bitartrate
on the contractility of the heart]. Ned Tijdschr Geneeskd. 1962 Sep 8;106:1800-5.
Dutch. PubMed PMID: 14472197.

4: USE OF metaraminol bitartrate as a vasopressor agent. J Am Med Assoc. 1957 Apr
20;163(16):1482. PubMed PMID: 13415915.

5: Bolzan AA, Laus JL, Nunes N, De Andrade CP. Effects of metaraminol bitartrate
on intraocular pressure in dogs under halothane anesthesia. Vet Ophthalmol.
1998;1(2-3):115-118. PubMed PMID: 11397219.

6: Martin CJ, Saxena SJ. High-performance liquid chromatographic determination of
metaraminol bitartrate in the presence of parabens. J Pharm Sci. 1980
Dec;69(12):1459-61. PubMed PMID: 7463342.

7: Weber JD. Fluorometric determination of metaraminol bitartrate injection. J
Assoc Off Anal Chem. 1978 Jul;61(4):949-50. PubMed PMID: 681269.

8: Bernstein A. Myocardial infarction induced by metaraminol bitartrate
(aramine). J Ir Med Assoc. 1966 Oct;59(352):127-8. PubMed PMID: 6009556.

9: SPOEREL WE, SELENY FL, WILLIAMSON RD. SHOCK CAUSED BY CONTINUOUS INFUSION OF
METARAMINOL BITARTRATE (ARAMINE). Can Med Assoc J. 1964 Feb 1;90:349-53. PubMed
PMID: 14122464; PubMed Central PMCID: PMC1922212.

10: TAYLOR WJ, LLEWELLYN-THOMAS E, DECANDOLE CA, MURPHY JB, SELLERS EA. The use of metaraminol bitartrate to reduce the side effects of atropine. Can Med Assoc
J. 1960 Jun 4;82:1147-51. PubMed PMID: 13837215; PubMed Central PMCID:
PMC1938444.

11: DIPPY WE, DORNEY ER. Tissue necrosis and slough produced by metaraminol
bitartrate. J Am Med Assoc. 1959 Aug 1;170(14):1647-8. PubMed PMID: 13672750.