Carcinine

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

MedKoo CAT#: 412333

CAS#: 56897-53-1

Description: Carcinine is a beta-alanine derivative that is the amide obtained by formal condensation of the carboxy group of beta-alanine with the primary amino group of histamine. It has a role as a crustacean metabolite and an antioxidant. It is a beta-alanine derivative, a monocarboxylic acid amide and a member of imidazoles. It derives from a histamine.


Chemical Structure

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Carcinine
CAS# 56897-53-1

Theoretical Analysis

MedKoo Cat#: 412333
Name: Carcinine
CAS#: 56897-53-1
Chemical Formula: C8H14N4O
Exact Mass: 182.1168
Molecular Weight: 182.23
Elemental Analysis: C, 52.73; H, 7.74; N, 30.75; O, 8.78

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Carcinine; UNIIWIV0W167TC; UNII WIV0W167TC; UNII-WIV0W167TC

IUPAC/Chemical Name: Propanamide, 3-amino-N-(2-(1H-imidazol-4-yl)ethyl)-

InChi Key: ANRUJJLGVODXIK-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H14N4O/c9-3-1-8(13)11-4-2-7-5-10-6-12-7/h5-6H,1-4,9H2,(H,10,12)(H,11,13)

SMILES Code: O=C(NCCC1=CNC=N1)CCN

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: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 182.23 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: Denno ME, Privman E, Borman RP, Wolin DC, Venton BJ. Quantification of Histamine and Carcinine in Drosophila melanogaster Tissues. ACS Chem Neurosci. 2016 Mar 16;7(3):407-14. doi: 10.1021/acschemneuro.5b00326. Epub 2016 Jan 28. PMID: 26765065; PMCID: PMC4798850.

2: Marchette LD, Wang H, Li F, Babizhayev MA, Kasus-Jacobi A. Carcinine has 4-hydroxynonenal scavenging property and neuroprotective effect in mouse retina. Invest Ophthalmol Vis Sci. 2012 Jun 20;53(7):3572-83. doi: 10.1167/iovs.11-9042. PMID: 22577078; PMCID: PMC3390180.

3: Stenesen D, Moehlman AT, Krämer H. The carcinine transporter CarT is required in Drosophila photoreceptor neurons to sustain histamine recycling. Elife. 2015 Dec 14;4:e10972. doi: 10.7554/eLife.10972. PMID: 26653853; PMCID: PMC4739767.

4: Chaturvedi R, Luan Z, Guo P, Li HS. Drosophila Vision Depends on Carcinine Uptake by an Organic Cation Transporter. Cell Rep. 2016 Mar 8;14(9):2076-2083. doi: 10.1016/j.celrep.2016.02.009. Epub 2016 Feb 25. PMID: 26923590; PMCID: PMC4785057.

5: Chen Z, Sakurai E, Hu W, Jin C, Kiso Y, Kato M, Watanabe T, Wei E, Yanai K. Pharmacological effects of carcinine on histaminergic neurons in the brain. Br J Pharmacol. 2004 Nov;143(5):573-80. doi: 10.1038/sj.bjp.0705978. Epub 2004 Oct 4. PMID: 15466447; PMCID: PMC1575432.

6: Gavin BA, Arruda SE, Dolph PJ. The role of carcinine in signaling at the Drosophila photoreceptor synapse. PLoS Genet. 2007 Dec;3(12):e206. doi: 10.1371/journal.pgen.0030206. PMID: 18069895; PMCID: PMC2134947.

7: Babizhayev MA. The detox strategy in smoking comprising nutraceutical formulas of non-hydrolyzed carnosine or carcinine used to protect human health. Hum Exp Toxicol. 2014 Mar;33(3):284-316. doi: 10.1177/0960327113493306. Epub 2013 Nov 12. PMID: 24220875.

8: Carroll L, Karton A, Radom L, Davies MJ, Pattison DI. Carnosine and Carcinine Derivatives Rapidly React with Hypochlorous Acid to Form Chloramines and Dichloramines. Chem Res Toxicol. 2019 Mar 18;32(3):513-525. doi: 10.1021/acs.chemrestox.8b00363. Epub 2019 Feb 15. PMID: 30693765.

9: Flancbaum L, Brotman DN, Fitzpatrick JC, Van Es T, Kasziba E, Fisher H. Existence of carcinine, a histamine-related compound, in mammalian tissues. Life Sci. 1990;47(17):1587-93. doi: 10.1016/0024-3205(90)90188-w. PMID: 2250571.

10: Arnould JM. Biosynthèse de la carcinine (beta-alanyl-histamine) in vivo [Biosynthesis of carcinine (beta-alanyl-histamine) in vivo]. Arch Int Physiol Biochim. 1985 Nov;93(4):351-61. French. doi: 10.3109/13813458509079616. PMID: 2421673.