Anisotropine Methylbromide
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MedKoo CAT#: 317194

CAS#: 80-50-2

Description: Octatropine methylbromide (INN) or anisotropine methylbromide (USAN), trade names Valpin, Endovalpin, Lytispasm and others, is a muscarinic antagonist and antispasmodic. It was introduced to the U.S. market in 1963 as an adjunct in the treatment of peptic ulcer, and promoted as being more specific to the gastrointestinal tract than other anticholinergics. Anisotropine methylbromide is a quaternary ammonium compound. Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents. Depending on the dose, anisotropine methylbromide may reduce the motility and secretory activity of the gastrointestinal system, and the tone of the ureter and urinary bladder and may have a slight relaxant action on the bile ducts and gallbladder. In general, smaller doses of anisotropine methylbromide inhibit salivary and bronchial secretions, sweating, and accommodation; cause dilatation of the pupil; and increase the heart rate. Larger doses are required to decrease motility of the gastrointestinal and urinary tracts and to inhibit gastric acid secretion.


Chemical Structure

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Anisotropine Methylbromide
CAS# 80-50-2

Theoretical Analysis

MedKoo Cat#: 317194
Name: Anisotropine Methylbromide
CAS#: 80-50-2
Chemical Formula: C17H32BrNO2
Exact Mass: 361.16164
Molecular Weight: 362.35
Elemental Analysis: C, 56.35; H, 8.90; Br, 22.05; N, 3.87; O, 8.83

Price and Availability

Size Price Availability Quantity
100.0mg USD 70.0 2 Weeks
200.0mg USD 90.0 2 Weeks
500.0mg USD 120.0 2 Weeks
1.0g USD 150.0 2 Weeks
2.0g USD 250.0 2 Weeks
5.0g USD 450.0 2 Weeks
10.0g USD 650.0 2 Weeks
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Synonym: Endovalpin; Lytispasm; Valpin; Methyloctatropine bromide; Anisotropine methobromide; Octatropine methylbromide

IUPAC/Chemical Name: [(1R,5S)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl] 2-propylpentanoate;bromide

InChi Key: QSFKGMJOKUZAJM-UHFFFAOYSA-M

InChi Code: InChI=1S/C17H32NO2.BrH/c1-5-7-13(8-6-2)17(19)20-16-11-14-9-10-15(12-16)18(14,3)4;/h13-16H,5-12H2,1-4H3;1H/q+1;/p-1

SMILES Code: CCCC(CCC)C(=O)OC1CC2CCC(C1)[N+]2(C)C.[Br-]

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, 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

Preparing Stock Solutions

The following data is based on the product molecular weight 362.35 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

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1: Freston JW, Forbes JA. A double-blind evaluation of the nocturnal antisecretory effects of anisotropine methylbromide in man. Dose response and duration of action studies. J Clin Pharmacol. 1977 Jan;17(1):29-36. PubMed PMID: 13090.

2: Abad Iglesias R. [Clinical study of the selectivity, tolerance and therapeutic status of anisotropine methylbromide and its combinations (Vapin Complex) in digestive pathology and in spastic changes of the biliary tract]. Folia Clin Int (Barc). 1973 May;23(5):382-402. Spanish. PubMed PMID: 4808337.

3: Pfeffer M, Schor JM. Intestinal sorption of anisotropine methylbromide in the rat. J Pharm Sci. 1972 Aug;61(8):1223-7. PubMed PMID: 5068340.

4: Nakayama K, Taira N, Hashimoto K, Kobayashi S, Kumakura S. Effects of anisotropine methylbromide (Valpin) and its mixture with sulpyrine on vocalization response and spasm of intestine induced by acetylcholine in dogs. Jpn J Pharmacol. 1972 Apr;22(2):215-20. PubMed PMID: 4538412.

5: Giovannelli CA, Vigo PL. [Anisotropine methylbromide (Valpin) in the treatment of spasms of the gastrointestinal system. Biometric study]. Minerva Med. 1970 Dec 22;61(102):5942-51. Italian. PubMed PMID: 5498741.

6: Kanda K. [Trials with anisotropine methylbromide (Valpin) in the radiography of the stomach]. Rinsho Hoshasen. 1968 Dec;13(12):1013-9. Japanese. PubMed PMID: 5191267.

7: Pfeffer M, Schor JM, Bolton S, Jacobsen R. Human urinary excretion of the quaternary ammonium compounds anisotropine methylbromide and propantheline bromide. J Pharm Sci. 1968 Aug;57(8):1375-8. PubMed PMID: 5695651.

8: Pfeffer M, Schor JM, Gluck N, Semmel MG, Griboff S. Human urinary excretion of orally administered anisotropine methylbromide. J Pharm Sci. 1968 Jan;57(1):36-8. PubMed PMID: 5694710.

9: Stiel JN, Baxter CH. The effect of anisotropine methylbromide on human saliva flow and gastric secretion. Med J Aust. 1967 May 27;1(21):1076-8. PubMed PMID: 6071739.

10: Bonney WW, Kaufman JJ. The effect of anisotropine methylbromide on bladder function. (A clinical study). West Med Med J West. 1967 Feb;8(2):40-1. PubMed PMID: 6072160.