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MedKoo Cat#: 592580 | Name: Metaraminol HCl

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 HCl
CAS#5967-52-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 592580

Name: Metaraminol HCl

CAS#: 5967-52-2 (HCl)

Chemical Formula: C9H14ClNO2

Exact Mass: 0.0000

Molecular Weight: 203.67

Elemental Analysis: C, 53.08; H, 6.93; Cl, 17.41; N, 6.88; O, 15.71

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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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 hydrochloride; Metaraminol HCl
IUPAC/Chemical Name
Benzyl alcohol, alpha-(1-aminoethyl)-m-hydroxy-, hydrochloride
InChi Key
PPRPRPMMKPXRKK-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H13NO2.ClH/c1-6(10)9(12)7-3-2-4-8(11)5-7;/h2-6,9,11-12H,10H2,1H3;1H
SMILES Code
OC1=CC(C(O)C(N)C)=CC=C1.[H]Cl
Appearance
Solid 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
Shelf Life
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 203.67 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
1: Hill DW, Hyde WG, Kind AJ, Greulich D, Hopkins S. Development of analytical methods for the detection of metaraminol in the horse. J Anal Toxicol. 2000 May-Jun;24(4):281-8. PubMed PMID: 10872576. 2: Johnson GE, Pugsley TA. Studies on the interrelationship between the syntheses of noradrenaline and metaraminol. Br J Pharmacol. 1970 May;39(1):167-74. PubMed PMID: 4317857; PubMed Central PMCID: PMC1702959. 3: Natalini G, Schivalocchi V, Rosano A, Taranto M, Pletti C, Bernardini A. Norepinephrine and metaraminol in septic shock: a comparison of the hemodynamic effects. Intensive Care Med. 2005 May;31(5):634-7. Epub 2005 Apr 1. PubMed PMID: 15803299. 4: Critchley LA, Yu SC. A comparative study of three different methods of administering metaraminol during spinal anaesthesia in the elderly. Anaesth Intensive Care. 2001 Apr;29(2):141-8. PubMed PMID: 11314833. 5: Block T, Sturm W, Ernst G, Staehler G, Schmiedt E. [Metaraminol in therapy of various forms of priapism]. Urologe A. 1988 Jul;27(4):225-9. German. PubMed PMID: 3140463. 6: Ngan Kee WD, Khaw KS, Lee BB, Wong MM, Ng FF. Metaraminol infusion for maintenance of arterial blood pressure during spinal anesthesia for cesarean delivery: the effect of a crystalloid bolus. Anesth Analg. 2001 Sep;93(3):703-8. PubMed PMID: 11524344. 7: Johnson GE, Pugsley TA. The formation and release of metaraminol during exposure to warm or cold environments. Br J Pharmacol. 1968 Oct;34(2):267-76. PubMed PMID: 5687587; PubMed Central PMCID: PMC1703345. 8: Shoji T, Sakurada S, Kisara K. [Effect of beta-phenylethylamine derivatives on the central nervous system. II. Pharmacological effect of the intracerebral administration of metaraminol on the central nervous system]. Nihon Yakurigaku Zasshi. 1975 Jan;71(1):1-10. Japanese. PubMed PMID: 1171807. 9: Tsai SK, Hong CY. Intracavernosal metaraminol for treatment of intraoperative penile erection. Postgrad Med J. 1990 Oct;66(780):831-3. PubMed PMID: 2099422; PubMed Central PMCID: PMC2429711. 10: Någren K, Halldin C, Swahn CG, Suhara T, Farde L. [11C]metaraminol, a false neurotransmitter: preparation, metabolite studies and positron emission tomography examination in monkey. Nucl Med Biol. 1996 Apr;23(3):221-7. PubMed PMID: 8782229. 11: Ngan Kee WD, Lau TK, Khaw KS, Lee BB. Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective cesarean section. Anesthesiology. 2001 Aug;95(2):307-13. PubMed PMID: 11506099. 12: 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. PubMed PMID: 2724688. 13: Critchley LA, Conway F. Hypotension during subarachnoid anaesthesia: haemodynamic effects of colloid and metaraminol. Br J Anaesth. 1996 May;76(5):734-6. PubMed PMID: 8688279. 14: Paton DM. Effects of Na+ and K+ on the uptake of metaraminol by rabbit ventricular slices. Br J Pharmacol. 1971 Jan;41(1):65-75. PubMed PMID: 4251250; PubMed Central PMCID: PMC1702743. 15: Johnson RG, Carty SE, Hayflick S, Scarpa A. Mechanisms of accumulation of tyramine, metaraminol, and isoproterenol in isolated chromaffin granules and ghosts. Biochem Pharmacol. 1982 Mar 1;31(5):815-23. PubMed PMID: 7082350. 16: Rashmi M, Swati D. In silico drug re-purposing against African sleeping sickness using GlcNAc-PI de-N-acetylase as an experimental target. Comput Biol Chem. 2015 Dec;59 Pt A:87-94. doi: 10.1016/j.compbiolchem.2015.09.010. Epub 2015 Sep 24. PubMed PMID: 26476127. 17: Kankkunen T, Huupponen I, Lahtinen K, Sundell M, Ekman K, Kontturi K, Hirvonen J. Improved stability and release control of levodopa and metaraminol using ion-exchange fibers and transdermal iontophoresis. Eur J Pharm Sci. 2002 Sep;16(4-5):273-80. PubMed PMID: 12208457. 18: Shoji T, Sakurada S, Kisara K. [Effect of beta-phenylethylamine derivatives on the central nervous system. III. Motor activity changes in mice due to the intracerebral administration of metaraminol]. Nihon Yakurigaku Zasshi. 1975 Jan;71(1):11-8. Japanese. PubMed PMID: 1171809. 19: Ahtee L, Saarnivaara L. The effect of narcotic analgesics on the uptake of 5-hydroxytryptamine and (-)-metaraminol by blood platelets. Br J Pharmacol. 1973 Apr;47(4):808-18. PubMed PMID: 4740642; PubMed Central PMCID: PMC1776065. 20: Anton AH, Berk AI. Distribution of metaraminol and its relation to norepinephrine. Eur J Pharmacol. 1977 Jul 15;44(2):161-7. PubMed PMID: 885165.

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