Coprine | CAS#58919-61-2 | toxin

MedKoo Cat#: 597283 | Name: Coprine

Description:

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

Coprine is a poisonous toxin that is found in mushrooms resulting in coprinus syndrome.

Chemical Structure

Coprine

CAS#58919-61-2

Theoretical Analysis

MedKoo Cat#: 597283

Name: Coprine

CAS#: 58919-61-2

Chemical Formula: C8H14N2O4

Exact Mass: 202.0954

Molecular Weight: 202.21

Elemental Analysis: C, 47.52; H, 6.98; N, 13.85; O, 31.65

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

Coprine;

IUPAC/Chemical Name

(1-hydroxycyclopropyl)-L-glutamine

InChi Key

OXSNIRUFWNKVQN-YFKPBYRVSA-N

InChi Code

InChI=1S/C8H14N2O4/c9-6(11)2-1-5(7(12)13)10-8(14)3-4-8/h5,10,14H,1-4H2,(H2,9,11)(H,12,13)/t5-/m0/s1

SMILES Code

O=C(N)CC[C@@H](C(O)=O)NC1(O)CC1

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 202.21 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: Kamijo Y. [Clinical toxicology of mushroom poisoning. Clitocybe clavipes, Coprinopsis atramentarius]. Chudoku Kenkyu. 2013 Sep;26(3):223-5. Review. Japanese. PubMed PMID: 24224386. 2: Haberl B, Pfab R, Berndt S, Greifenhagen C, Zilker T. Case series: Alcohol intolerance with Coprine-like syndrome after consumption of the mushroom Lepiota aspera (Pers.:Fr.) Quél., 1886 (Freckled Dapperling). Clin Toxicol (Phila). 2011 Feb;49(2):113-4. doi: 10.3109/15563650.2011.554840. PubMed PMID: 21370948. 3: Saviuc P, Flesch F. [Acute higher funghi mushroom poisoning and its treatment]. Presse Med. 2003 Sep 20;32(30):1427-35. Review. French. PubMed PMID: 14534493. 4: Hender E, May T, Beulke S. Poisoning due to eating fungi in Victoria. Aust Fam Physician. 2000 Oct;29(10):1000-4. PubMed PMID: 11059094. 5: Marty H. [Of mushrooms and alcohol]. Schweiz Med Wochenschr. 1998 Apr 11;128(15):598. German. PubMed PMID: 9679002. 6: Matthies L, Laatsch H. [An unusual mushroom mycotoxin: coprine, a deterrent to alcohol abuse]. Pharm Unserer Zeit. 1992 Jan;21(1):14-20. German. PubMed PMID: 1553385. 7: Michelot D. Poisoning by Coprinus atramentarius. Nat Toxins. 1992;1(2):73-80. Review. PubMed PMID: 1344910. 8: Nilsson GE, Tottmar O. Effects of disulfiram and coprine on rat brain tryptophan hydroxylation in vivo. Neurochem Res. 1989 Jun;14(6):537-40. PubMed PMID: 2474765. 9: Helander A, Tottmar O. Effects of disulfiram, cyanamide and 1-aminocyclopropanol on the aldehyde dehydrogenase activity in human erythrocytes and leukocytes. Pharmacol Toxicol. 1988 Oct;63(4):262-5. PubMed PMID: 2848231. 10: Zilker T. [Diagnosis and therapy of mushroom poisoning (II)]. Leber Magen Darm. 1987 Jul;17(3):173-97. German. PubMed PMID: 3613814. 11: Nilsson GE, Tottmar O. Effects of biogenic aldehydes and aldehyde dehydrogenase inhibitors on rat brain tryptophan hydroxylase activity in vitro. Brain Res. 1987 Apr 21;409(2):374-9. PubMed PMID: 2438010. 12: Nilsson GE, Tottmar O, Wahlström G. Effects of aldehyde dehydrogenase inhibitors on hexobarbital sensitivity and neuroamine metabolism in rat brain. Brain Res. 1987 Apr 21;409(2):265-74. PubMed PMID: 2438009. 13: Hellström E, Tottmar O. Effects of aldehyde dehydrogenase inhibitors on enzymes involved in the metabolism of biogenic aldehydes in rat liver and brain. Biochem Pharmacol. 1982 Dec 1;31(23):3899-905. PubMed PMID: 7159468. 14: Pettersson H, Tottmar O. Inhibition of aldehyde dehydrogenases in rat brain and liver by disulfiram and coprine. J Neurochem. 1982 Sep;39(3):628-34. PubMed PMID: 7097272. 15: DiPalma JR. Mushroom poisoning. Am Fam Physician. 1981 May;23(5):169-72. PubMed PMID: 7234633. 16: Sinclair JD, Lindros KO, Terho K. Aldehyde dehydrogenase inhibitors and voluntary ethanol drinking by rats. Adv Exp Med Biol. 1980;132:481-7. PubMed PMID: 7424727. 17: Fried R. Biochemical actions of anti-alcoholic agents. Subst Alcohol Actions Misuse. 1980;1(1):5-27. Review. PubMed PMID: 6275559. 18: Tottmar O, Hellström E. Blood pressure response to ethanol in relation to acetaldehyde levels and dopamine-beta-hydroxylase activity in rats pretreated with disulfiram, cyanamide and coprine. Acta Pharmacol Toxicol (Copenh). 1979 Oct;45(4):272-81. PubMed PMID: 525358. 19: Wiseman JS, Abeles RH. Mechanism of inhibition of aldehyde dehydrogenase by cyclopropranone hydrate and the mushroom toxin coprine. Biochemistry. 1979 Feb 6;18(3):427-35. PubMed PMID: 369602. 20: Jönsson M, Lindquist NG, Plöen L, Ekvärn S, Kronevi T. Testicular lesions of coprine and benzcoprine. Toxicology. 1979 Feb;12(2):89-100. PubMed PMID: 473235.