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
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.
| 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: 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.
