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MedKoo Cat#: 597605 | Name: Met-enkephalinamide

Description:

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

Met-enkephalinamide is a potent Met-enkephalin analog, and a potent, long-lasting synthetic pentapeptide analgesic.

Chemical Structure

Met-enkephalinamide
CAS#60117-17-1

Theoretical Analysis

MedKoo Cat#: 597605

Name: Met-enkephalinamide

CAS#: 60117-17-1

Chemical Formula: C27H36N6O6S

Exact Mass: 572.2417

Molecular Weight: 572.68

Elemental Analysis: C, 56.63; H, 6.34; N, 14.68; O, 16.76; S, 5.60

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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Related CAS #
No Data
Synonym
Met-enkephalinamide; Enkephalinamide-met-; Methionine enkephalinamide;
IUPAC/Chemical Name
(S)-2-((S)-2-(2-(2-((S)-2-amino-3-(4-hydroxyphenyl)propanamido)acetamido)acetamido)-3-phenylpropanamido)-4-(methylthio)butanamide
InChi Key
HBDDEVHKKBWEQT-FKBYEOEOSA-N
InChi Code
InChI=1S/C27H36N6O6S/c1-40-12-11-21(25(29)37)33-27(39)22(14-17-5-3-2-4-6-17)32-24(36)16-30-23(35)15-31-26(38)20(28)13-18-7-9-19(34)10-8-18/h2-10,20-22,34H,11-16,28H2,1H3,(H2,29,37)(H,30,35)(H,31,38)(H,32,36)(H,33,39)/t20-,21-,22-/m0/s1
SMILES Code
CSCC[C@@H](C(N)=O)NC([C@H](CC1=CC=CC=C1)NC(CNC(CNC([C@H](CC2=CC=C(O)C=C2)N)=O)=O)=O)=O
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 572.68 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: Flórez J, Mediavilla A, Pazos A. Respiratory effects of beta-endorphin, D-Ala2-met-enkephalinamide, and Met-enkephalin injected into the lateral ventricle and the pontomedullary subarachnoid space. Brain Res. 1980 Oct 13;199(1):197-206. PubMed PMID: 7407621. 2: Owen MD, Gisolfi CV, Reynolds DG, Gurll NJ. Autonomic effects of central injections of D-Ala2-Met-enkephalinamide (DAME) in the conscious monkey. Peptides. 1984 Jul-Aug;5(4):737-42. PubMed PMID: 6494024. 3: Pert CB, Pert A, Chang JK, Fong BT. (D-Ala2)-Met-enkephalinamide: a potent, long-lasting synthetic pentapeptide analgesic. Science. 1976 Oct 15;194(4262):330-2. PubMed PMID: 968485. 4: Izumi K, Munekata E, Yamamoto H, Nakanishi T, Barbeau A. Effects of taurine and gamma-aminobutyric acid on akinesia and analgesia induced by D-Ala2-Met-enkephalinamide in rats. Peptides. 1980 Summer;1(2):139-46. PubMed PMID: 7243612. 5: Herman ZS, Kowalski J. Effect of D-Ala2-met-enkephalinamide and morphine on the activity of choline acetyltransferase and acetylcholinesterase in rat brain. Acta Physiol Pol. 1981 May-Jun;32(3):233-7. PubMed PMID: 7304195. 6: Stanton TL, Sartin NF, Beckman AL. Changes in body temperature and metabolic rate following microinjection of Met-enkephalinamide in the preoptic/anterior hypothalamus of rats. Regul Pept. 1985 Nov 28;12(4):333-43. PubMed PMID: 3867098. 7: Higashijima T, Kobayashi J, Nagai U, Miyazawa T. Nuclear-magnetic-resonance study on Met-enkephalin and Met-enkephalinamide. Molecular association and conformation. Eur J Biochem. 1979 Jun;97(1):43-57. PubMed PMID: 38962. 8: Cripps MM, Patchen-Moor K. Inhibition of stimulated lacrimal secretion by [D-Ala2]Met-enkephalinamide. Am J Physiol. 1989 Jul;257(1 Pt 1):G151-6. PubMed PMID: 2546441. 9: Guaza C, Borrell J. The Met-enkephalin analog D-Ala2-Met-enkephalinamide decreases the adrenocortical response to ACTH in dispersed rat adrenal cells. Peptides. 1984 Sep-Oct;5(5):895-7. PubMed PMID: 6095218. 10: Schroeder JA, Schneider JS. GABA-opioid interactions in the globus pallidus: [D-Ala2]-Met-enkephalinamide attenuates potassium-evoked GABA release after nigrostriatal lesion. J Neurochem. 2002 Aug;82(3):666-73. PubMed PMID: 12153490. 11: De Souza EB, Van Loon GR. D-Ala2-Met-enkephalinamide, a potent opioid peptide, alters pituitary-adrenocortical secretion in rats. Endocrinology. 1982 Nov;111(5):1483-90. PubMed PMID: 6290184. 12: Hansson E. Accumulation of putative amino acid neurotransmitters, monoamines and D-Ala2-Met-enkephalinamide in primary astroglial cultures from various brain areas, visualized by autoradiography. Brain Res. 1983 Dec 19;289(1-2):189-96. PubMed PMID: 6140983. 13: Oitzl MS, Huston JP. Electroencephalographic spreading depression and concomitant behavioral changes induced by intrahippocampal injections of ACTH1-24 and D-Ala2-Met-enkephalinamide in the rat. Brain Res. 1984 Aug 6;308(1):33-42. PubMed PMID: 6089954. 14: Ferretti ME, Borasio PG, Biondi C, Capuzzo A, Fabbri E, Pareschi MC. Interactions between prostaglandin E2 and D-ala2-met-enkephalinamide on adenylate cyclase activity in the guinea-pig superior cervical ganglion. Neurochem Res. 1988 Sep;13(9):797-802. PubMed PMID: 3226463. 15: Van Loon GR, Appel NM. Plasma norepinephrine, epinephrine and dopamine responses to intracerebral administration of a met-enkephalin analog, D-ala2-met-enkephalinamide, in rats. Neuroendocrinology. 1981 Sep;33(3):153-7. PubMed PMID: 6270584. 16: Brus R, Szkilnik R, Krzeminski T, Juraszczyk Z, Kurcok A, Herman ZS. Central effects of D-Ala2-met-enkephalinamide on the blood pressure of rats after central chemical sympathectomy or serotoninectomy. Biomed Biochim Acta. 1985;44(5):779-83. PubMed PMID: 4062924. 17: Bugajski J, Turoón M, Gadek-Michalska A, Ołowska A. Influence of the central histaminergic systems on the pituitary-adrenocortical response to met-enkephalinamide. J Physiol Pharmacol. 1995 Sep;46(3):313-22. PubMed PMID: 8527812. 18: Bergasa NV, Zhou J, Ravi J, Shi Q. The opioid peptide analog D-Ala2-Met-enkephalinamide decreases bile flow by a central mechanism. Peptides. 1999;20(8):979-86. PubMed PMID: 10503777. 19: Huang JT. Accumulation of amino acids, met-enkephalinamide and morphine in choroid plexus: effect of pretreatment with phosphatidylcholine vesicles. Res Commun Chem Pathol Pharmacol. 1980 Jun;28(3):567-70. PubMed PMID: 7403669. 20: Ukponmwan OE, van der Poel-Heisterkamp AL, Haffmans J, Dzoljic M. MAO-B inhibitor deprenyl and beta-phenylethylamine potentiate [D-ALA2]-Met-enkephalinamide-induced seizures. Naunyn Schmiedebergs Arch Pharmacol. 1983 Feb;322(1):38-41. PubMed PMID: 6405286.

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