MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 318195 | Name: Metaraminol Bitartrate
Featured New

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Metaraminol is a selective α₁-adrenergic receptor agonist with vasoconstrictive properties. It primarily increases blood pressure by inducing peripheral vasoconstriction, making it useful in treating hypotension during anesthesia or shock. Additionally, metaraminol has some indirect sympathomimetic activity by stimulating norepinephrine release, further enhancing its pressor effects. Unlike direct-acting catecholamines, it has a longer duration of action due to slower metabolism.

Chemical Structure

Metaraminol Bitartrate
CAS#33402-03-8 (tartrate)

Theoretical Analysis

MedKoo Cat#: 318195

Name: Metaraminol Bitartrate

CAS#: 33402-03-8 (tartrate)

Chemical Formula: C13H19NO8

Exact Mass: 0.0000

Molecular Weight: 317.29

Elemental Analysis: C, 49.21; H, 6.04; N, 4.41; O, 40.34

Price and Availability

Size Price Availability Quantity
1g USD 150.00 Ready to ship
2g USD 250.00 Ready to ship
5g USD 550.00 Ready to ship
10g USD 950.00 Ready to ship
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
33402-03-8 (tartrate) 54-49-9 (free base) 5967-52-2 (HCl) 5967-53-3 (oxalate dihydrate)
Synonym
Aramine; Icoral B; Metaradrine bitartrate; Metaraminol bitartrate; Metaraminol hydrogen tartrate; Metaraminol tartrate; Pressorol
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/
Solvent mg/mL mM comments
Solubility
DMSO 0.0 0.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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
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.