Fmrfamide | CAS#64190-70-1 | molluscan neuroactive peptide

MedKoo Cat#: 597717 | Name: Fmrfamide

Description:

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

Fmrfamide is a molluscan neuroactive peptide which induces a fast excitatory depolarizing response due to direct activation of amiloride-sensitive SODIUM CHANNELS.

Chemical Structure

Fmrfamide

CAS#64190-70-1

Theoretical Analysis

MedKoo Cat#: 597717

Name: Fmrfamide

CAS#: 64190-70-1

Chemical Formula: C29H42N8O4S

Exact Mass: 598.3050

Molecular Weight: 598.76

Elemental Analysis: C, 58.17; H, 7.07; N, 18.71; O, 10.69; S, 5.35

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

Fmrfamide;

IUPAC/Chemical Name

(S)-N-((S)-1-amino-1-oxo-3-phenylpropan-2-yl)-2-((S)-2-((S)-2-amino-3-phenylpropanamido)-4-(methylthio)butanamido)-5-guanidinopentanamide

InChi Key

WCSPDMCSKYUFBX-ZJZGAYNASA-N

InChi Code

InChI=1S/C29H42N8O4S/c1-42-16-14-23(35-26(39)21(30)17-19-9-4-2-5-10-19)28(41)36-22(13-8-15-34-29(32)33)27(40)37-24(25(31)38)18-20-11-6-3-7-12-20/h2-7,9-12,21-24H,8,13-18,30H2,1H3,(H2,31,38)(H,35,39)(H,36,41)(H,37,40)(H4,32,33,34)/t21-,22-,23-,24-/m0/s1

SMILES Code

O=C(N)[C@H](CC1=CC=CC=C1)NC([C@H](CCCNC(N)=N)NC([C@H](CCSC)NC([C@H](CC2=CC=CC=C2)N)=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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 598.76 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: Hillyer JF, Estévez-Lao TY, de la Parte LE. Myotropic effects of FMRFamide containing peptides on the heart of the mosquito Anopheles gambiae. Gen Comp Endocrinol. 2014 Jun 1;202:15-25. doi: 10.1016/j.ygcen.2014.03.048. Epub 2014 Apr 18. PubMed PMID: 24747482. 2: Lenz O, Xiong J, Nelson MD, Raizen DM, Williams JA. FMRFamide signaling promotes stress-induced sleep in Drosophila. Brain Behav Immun. 2015 Jul;47:141-8. doi: 10.1016/j.bbi.2014.12.028. Epub 2015 Feb 7. PubMed PMID: 25668617; PubMed Central PMCID: PMC4467992. 3: Nelson MD, Lee KH, Churgin MA, Hill AJ, Van Buskirk C, Fang-Yen C, Raizen DM. FMRFamide-like FLP-13 neuropeptides promote quiescence following heat stress in Caenorhabditis elegans. Curr Biol. 2014 Oct 20;24(20):2406-10. doi: 10.1016/j.cub.2014.08.037. Epub 2014 Sep 25. PubMed PMID: 25264253; PubMed Central PMCID: PMC4254296. 4: Krajniak KG. Invertebrate FMRFamide related peptides. Protein Pept Lett. 2013 Jun;20(6):647-70. Review. PubMed PMID: 22630125. 5: Terenina NB, Kreshchenko ND, Chilyuta NV, Zaripova FF. [Serotonin and neuropeptide FMRFamide in the nervous system of Opisthioglyphe ranae (Trematoda: Plagiorchiidae). an immunocytochemical study]. Zh Evol Biokhim Fiziol. 2015 Mar-Apr;51(2):127-32. Russian. PubMed PMID: 26027387. 6: Li C, Timbers TA, Rose JK, Bozorgmehr T, McEwan A, Rankin CH. The FMRFamide-related neuropeptide FLP-20 is required in the mechanosensory neurons during memory for massed training in C. elegans. Learn Mem. 2013 Jan 16;20(2):103-8. doi: 10.1101/lm.028993.112. PubMed PMID: 23325727; PubMed Central PMCID: PMC3549060. 7: Sedra L, Lange AB. The female reproductive system of the kissing bug, Rhodnius prolixus: arrangements of muscles, distribution and myoactivity of two endogenous FMRFamide-like peptides. Peptides. 2014 Mar;53:140-7. doi: 10.1016/j.peptides.2013.04.003. Epub 2013 Apr 15. PubMed PMID: 23598080. 8: D'Aniello B, Polese G, Luongo L, Scandurra A, Magliozzi L, Aria M, Pinelli C. Neuroanatomical relationships between FMRFamide-immunoreactive components of the nervus terminalis and the topology of olfactory bulbs in teleost fish. Cell Tissue Res. 2016 Apr;364(1):43-57. doi: 10.1007/s00441-015-2295-4. Epub 2015 Oct 9. PubMed PMID: 26453401. 9: Shun'kina KV, Starunov VV, Zaitseva OV, Ostrovskii AN. Serotonin and FMRFamide immunoreactive elements in the nervous system of freshwater bryozoans (Bryozoa: Phylactolaemata). Dokl Biol Sci. 2013 Jul-Aug;451:244-7. doi: 10.1134/S0012496613040108. Epub 2013 Aug 24. PubMed PMID: 23975468. 10: Masler EP. A comparison of the FMRFamide-like peptide proteolytic activities of preparations from two plant-parasitic nematodes (Heterodera glycines and Meloidogyne incognita): possible targets for novel control. J Helminthol. 2013 Mar;87(1):71-7. doi: 10.1017/S0022149X12000053. Epub 2012 Feb 6. PubMed PMID: 22310027. 11: Shabelnikov S. Nerve-granular cell communication in the atrium of the snail Achatina achatina occurs via the cardioexcitatory transmitters serotonin and FMRFamide. Cell Tissue Res. 2016 Nov;366(2):245-254. doi: 10.1007/s00441-016-2483-x. Epub 2016 Sep 23. PubMed PMID: 27660155. 12: Cummins SF, Tollenaere A, Degnan BM, Croll RP. Molecular analysis of two FMRFamide-encoding transcripts expressed during the development of the tropical abalone Haliotis asinina. J Comp Neurol. 2011 Jul 1;519(10):2043-59. doi: 10.1002/cne.22621. PubMed PMID: 21452226. 13: Rőszer T, Bánfalvi G. FMRFamide-related peptides: anti-opiate transmitters acting in apoptosis. Peptides. 2012 Mar;34(1):177-85. doi: 10.1016/j.peptides.2011.04.011. Epub 2011 Apr 15. Review. PubMed PMID: 21524675. 14: Lee MG, Park JY, Park YK, Undem BJ. Direct activation of guinea pig vagal afferent neurons by FMRFamide. Neuroreport. 2011 Aug 24;22(12):609-12. doi: 10.1097/WNR.0b013e3283495a6e. PubMed PMID: 21734611; PubMed Central PMCID: PMC3136801. 15: Kobayashi S, Hattori M, Elekes K, Ito E, Matsuo R. FMRFamide regulates oscillatory activity of the olfactory center in the slug. Eur J Neurosci. 2010 Oct;32(7):1180-92. doi: 10.1111/j.1460-9568.2010.07399.x. Epub 2010 Aug 26. PubMed PMID: 20796020. 16: Kreshchenko N, Tolstenkov OO. Some aspects of the immunolocalization of FMRFamide in the nervous system of turbellarians, Polycelis tenuis and Girardia tigrina. Short communication. Acta Biol Hung. 2012;63 Suppl 2:83-7. doi: 10.1556/ABiol.63.2012.Suppl.2.10. PubMed PMID: 22776478. 17: Wollesen T, Cummins SF, Degnan BM, Wanninger A. FMRFamide gene and peptide expression during central nervous system development of the cephalopod mollusk, Idiosepius notoides. Evol Dev. 2010 Mar-Apr;12(2):113-30. doi: 10.1111/j.1525-142X.2010.00398.x. PubMed PMID: 20433453. 18: Green KA, Cottrell GA. Block of the helix FMRFamide-gated Na+ channel by FMRFamide and its analogues. J Physiol. 1999 Aug 15;519 Pt 1:47-56. PubMed PMID: 10432338; PubMed Central PMCID: PMC2269487. 19: Kodani Y, Furukawa Y. Position 552 in a FMRFamide-gated Na(+) channel affects the gating properties and the potency of FMRFamide. Zoolog Sci. 2010 May;27(5):440-8. doi: 10.2108/zsj.27.440. PubMed PMID: 20443692. 20: Lingueglia E, Deval E, Lazdunski M. FMRFamide-gated sodium channel and ASIC channels: a new class of ionotropic receptors for FMRFamide and related peptides. Peptides. 2006 May;27(5):1138-52. Epub 2006 Mar 3. Review. PubMed PMID: 16516345.