MedKoo Cat#: 597718 | Name: FK 33-824

Description:

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

FK 33-824 is a stable synthetic analog of methionine enkephalin (ENKEPHALIN, METHIONINE). Actions are similar to those of methionine enkephalin. Its effects can be reversed by narcotic antagonists such as naloxone.

Chemical Structure

FK 33-824
FK 33-824
CAS#64854-64-4

Theoretical Analysis

MedKoo Cat#: 597718

Name: FK 33-824

CAS#: 64854-64-4

Chemical Formula: C29H41N5O7S

Exact Mass: 603.2727

Molecular Weight: 603.73

Elemental Analysis: C, 57.69; H, 6.85; N, 11.60; O, 18.55; S, 5.31

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.
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Synonym
FK 33-824; FK-33-824; FK33-824; SAN 33-824; Damme; Sandoz FK 33-824;
IUPAC/Chemical Name
(2S)-N-(L-tyrosyl-D-alanylglycyl)-2-(((2S)-1-hydroxy-4-(methylsulfinyl)butan-2-yl)(methyl)amino)-3-phenylpropanamide
InChi Key
PKMZOKPYGPSHPV-IQNHEXCWSA-N
InChi Code
InChI=1S/C29H41N5O7S/c1-19(32-28(39)24(30)15-21-9-11-23(36)12-10-21)27(38)31-17-26(37)33-29(40)25(16-20-7-5-4-6-8-20)34(2)22(18-35)13-14-42(3)41/h4-12,19,22,24-25,35-36H,13-18,30H2,1-3H3,(H,31,38)(H,32,39)(H,33,37,40)/t19-,22+,24+,25+,42?/m1/s1
SMILES Code
O=C(NC(CNC([C@@H](C)NC([C@H](CC1=CC=C(O)C=C1)N)=O)=O)=O)[C@H](CC2=CC=CC=C2)N([C@H](CO)CCS(C)=O)C
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 603.73 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
1: Kaminski T. The involvement of protein kinases in signalling of opioid agonist FK 33-824 in porcine granulosa cells. Anim Reprod Sci. 2006 Jan;91(1-2):107-22. Epub 2005 Apr 25. PubMed PMID: 16310101. 2: Demura R, Suda T, Wakabayashi I, Yoshimura M, Jibiki K, Odagiri E, Demura H, Shizume K. Plasma pituitary hormone responses to the synthetic enkephalin analog (FK 33-824) in normal subjects and patients with pituitary diseases. J Clin Endocrinol Metab. 1981 Feb;52(2):263-6. PubMed PMID: 7462391. 3: Peñalva A, Villanueva L, Casanueva F, Cavagnini F, Gomez-Pan A, Müller EE. Cholinergic and histaminergic involvement in the growth hormone releasing effect of an enkephalin analog FK 33-824 in man. Psychopharmacology (Berl). 1983;80(2):120-4. PubMed PMID: 6308703. 4: Scheurer U, Drack E, Varga L, Halter F. Morphine-like action of enkephalin analog FK 33-824 on motility of the isolated rat colon. J Pharmacol Exp Ther. 1981 Nov;219(2):534-9. PubMed PMID: 7288632. 5: Clark WG, Bernardini GL, Ponder SW. Extreme hyperthermia induced in cats by the enkephalin analog FK 33-824. Pharmacol Biochem Behav. 1982 Jun;16(6):989-93. PubMed PMID: 6287503. 6: Bevilacqua M, Vago T, Raggi U, Scorza D, Proverbio M, Malacco E, Norbiato G. In vitro steroidogenic properties of FK 33 824, a stable analog of methionine-enkephalin. Opiate-dopamine interaction in the control of aldosterone production. J Endocrinol Invest. 1982 Sep-Oct;5(5):277-80. PubMed PMID: 6296218. 7: Kaminski T, Siawrys G, Okrasa S, Przala J. Action of the opioid agonist FK 33-824 on porcine small and large luteal cells from the mid-luteal phase: effect on progesterone, cAMP, cGMP and inositol phosphate release. Anim Reprod Sci. 1999 Aug 16;56(3-4):245-57. PubMed PMID: 10497920. 8: del Pozo E, von Graffenried B, Brownell J, Derrer F, Marbach P. Endocrine effect of a methionine-enkephalin derivative (FK 33-824) in man. Horm Res. 1980;13(2):90-7. PubMed PMID: 6262206. 9: Gouardères C, Beaudet A, Zajac JM, Cros J, Quirion R. High resolution radioautographic localization of [125I]FK-33-824-labelled mu opioid receptors in the spinal cord of normal and deafferented rats. Neuroscience. 1991;43(1):197-209. PubMed PMID: 1717884. 10: Allolio B, Deuss U, Kaulen D, Leonhardt U, Kallabis D, Hamel E, Winkelmann W. FK 33-824, a met-enkephalin analog, blocks corticotropin-releasing hormone-induced adrenocorticotropin secretion in normal subjects but not in patients with Cushing's disease. J Clin Endocrinol Metab. 1986 Dec;63(6):1427-31. PubMed PMID: 3023423. 11: Edens FW, Parkhurst CR. Plasma growth hormone and prolactin response to FK 33-824, a synthetic opioid agonist, in broiler chickens. Poult Sci. 1994 Nov;73(11):1746-54. PubMed PMID: 7862614. 12: Kaminski T. The response of phospholipase C/protein kinase C and adenylyl cyclase/protein kinase A pathways in porcine theca interna cells to opioid agonist FK 33-824. Domest Anim Endocrinol. 2004 Nov;27(4):379-96. PubMed PMID: 15519041. 13: Kaakkola S. Contralateral circling behaviour induced by intranigral injection of morphine and enkephalin analogue FK 33-824 in rats. Acta Pharmacol Toxicol (Copenh). 1980 Nov;47(5):385-93. PubMed PMID: 7197458. 14: Capogna M, Gähwiler BH, Thompson SM. Mechanism of mu-opioid receptor-mediated presynaptic inhibition in the rat hippocampus in vitro. J Physiol. 1993 Oct;470:539-58. PubMed PMID: 8308742; PubMed Central PMCID: PMC1143933. 15: Gosselin RE, Blankstein J, Dent DW, Hobson WC, Fuller GB, Reyes FI, Winter JS, Faiman C. Effects of naloxone and an enkephalin analog on serum prolactin, cortisol, and gonadotropins in the chimpanzee. Endocrinology. 1983 Jun;112(6):2168-73. PubMed PMID: 6406210. 16: Kandasamy SB, Williams BA. Hyperthermic effects of centrally injected (D-ala2, N-Me-Phe4, Met-(O)5-ol)-enkephalin (FK 33-824) in rabbits and guinea-pigs. Neuropharmacology. 1983 Oct;22(10):1177-81. PubMed PMID: 6316191. 17: Tremeau O, Faure G, Boulain JC, Bouet F, Menez A, Lecocq G, Morgat JL, Fromageot P. [Binding of a tritiated enkephalinergic analog (FK 33-824) to a mitochondrial fraction of rat brain]. Biochimie. 1981 Jun;63(6):477-84. French. PubMed PMID: 6266515. 18: Fjellner B, Hägermark O. Potentiation of histamine-induced itch and flare responses in human skin by the enkephalin analogue FK-33-824, beta-endorphin and morphine. Arch Dermatol Res. 1982;274(1-2):29-37. PubMed PMID: 6187298. 19: Jungkunz G, Nedopil N, Rüther E. Methysergide decreases prolactin release after FK 33-824 [Tyr-D-Ala-Gly-MePhe-Met(o)-ol], a potent analogue of methionine enkephalin. A study in man. Psychopharmacology (Berl). 1984;83(2):210-2. PubMed PMID: 6431476. 20: Zetler G, Raberg A. Ceruletide inhibits water intake in deprived mice: comparison with morphine and the enkephalin analogue, FK 33-824. Eur J Pharmacol. 1985 Aug 27;114(3):247-51. PubMed PMID: 2998807.