Metiamide | CAS#34839-70-8 | histamine H2 receptor antagonist

MedKoo Cat#: 326776 | Name: Metiamide

Description:

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

Metiamide is a histamine H2 receptor antagonist developed from another H2 antagonist, burimamide. It was an intermediate compound in the development of the successful anti-ulcer drug cimetidine (Tagamet).

Chemical Structure

Metiamide

CAS#34839-70-8

Theoretical Analysis

MedKoo Cat#: 326776

Name: Metiamide

CAS#: 34839-70-8

Chemical Formula: C9H16N4S2

Exact Mass: 244.0816

Molecular Weight: 244.38

Elemental Analysis: C, 44.23; H, 6.60; N, 22.93; S, 26.24

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

NSC 307755; SK&F 92058; SKF 92058; Metiamide.

IUPAC/Chemical Name

1-methyl-3-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)thiourea

InChi Key

FPBPLBWLMYGIQR-UHFFFAOYSA-N

InChi Code

InChI=1S/C9H16N4S2/c1-7-8(13-6-12-7)5-15-4-3-11-9(14)10-2/h6H,3-5H2,1-2H3,(H,12,13)(H2,10,11,14)

SMILES Code

S=C(NCCSCC1=C(C)NC=N1)NC

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

>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

After discovering that burimamide is largely inactive at physiological pH, due to the presence of its electron-donating side chain, the following steps were undertaken to stabilize burimamide: (1) addition of a sulfide group close to the imidazole ring, giving thiaburimamide; (2) addition of methyl group to the 4-position on the imidazole ring to favour the tautomer of thiaburimamide which binds better to the H2 receptor. These changes increased the bioavailability metiamide so that it is 10 times more potent than burimamide in inhibiting histamine-stimulated release of gastric acid. The clinical trials that began in 1973 demonstrated the ability of metiamide to provide symptomatic relief for ulcerous patients by increasing healing rate of peptic ulcers. However, during these trials, an unacceptable number of patients dosed with metiamide developed agranulocytosis (decreased white blood cell count).

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 244.38 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.

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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