Melanotan II

Melanotan II
Names
Pronunciation /mɛˈlænoʊtæn/ ⓘ
Systematic IUPAC name
L-Lysinamide, N-acetyl-L-norleucyl-L-alpha-aspartyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophyl-, cyclic (2-7)-peptide
Other names
List of other names
  • Ac-Nle-cyclo[Asp-His-D-Phe-Arg-Trp-Lys]-NH2
  • Ac-Nle-c[Asp-His-D-Phe-Arg-Trp-Lys]-NH2
  • Ac-cyclo[Nle4, Asp5,D-Phe7, Lys10]α-MSH4–10-NH2
  • N-Acetyl-L-norleucyl-L-α-aspartyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophyl-L-lysinamide (2→7)-lactam
  • MT-II
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
MeSH melanotan-II
UNII
  • InChI=1S/C50H69N15O9/c1-3-4-16-36(59-29(2)66)44(69)65-41-25-42(67)55-20-11-10-18-35(43(51)68)60-47(72)39(23-31-26-57-34-17-9-8-15-33(31)34)63-45(70)37(19-12-21-56-50(52)53)61-46(71)38(22-30-13-6-5-7-14-30)62-48(73)40(64-49(41)74)24-32-27-54-28-58-32/h5-9,13-15,17,26-28,35-41,57H,3-4,10-12,16,18-25H2,1-2H3,(H2,51,68)(H,54,58)(H,55,67)(H,59,66)(H,60,72)(H,61,71)(H,62,73)(H,63,70)(H,64,74)(H,65,69)(H4,52,53,56)/t35-,36-,37-,38+,39-,40-,41-/m0/s1 checkY
    Key: JDKLPDJLXHXHNV-MFVUMRCOSA-N checkY
  • CCCC[C@@H](C(=O)N[C@H]1CC(=O)NCCCC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CC2=CN=CN2)CC3=CC=CC=C3)CCCN=C(N)N)CC4=CNC5=CC=CC=C54)C(=O)N)NC(=O)C
Properties
C50H69N15O9
Molar mass 1024.180
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Structure of melanotan II (full size)

Melanotan II is a synthetic analogue of the peptide hormone α-melanocyte-stimulating hormone (α-MSH) that stimulates melanogenesis and increases sexual arousal.

It was under development as drug candidate for female sexual dysfunction and erectile dysfunction but clinical development ceased by 2003, and as of 2018, no product containing melanotan II was marketed and all commercial development had ceased.[1]

Unlicensed, untested, or fraudulent products sold as "melanotan II" are found on the Internet, and purported to be effective as "tanning drugs", though side effects such as uneven pigmentation (it makes already uneven pigmentation more noticeable), new nevi (moles), and darkening or enlargement of existing moles have been reported and have led to medical authorities discouraging its use. There has been no scientific study into the long term and permanent side effects the use of this peptide may cause.[2][3]

  1. ^ "Melanotan II". AdisInsight. Retrieved 13 Jan 2018.
  2. ^ Brennan R, Wells JS, Van Hout MC (September 2017). "The injecting use of image and performance-enhancing drugs (IPED) in the general population: a systematic review". Health & Social Care in the Community. 25 (5): 1459–1531. doi:10.1111/hsc.12326. PMID 26806443. S2CID 20159129.
  3. ^ Habbema L, Halk AB, Neumann M, Bergman W (October 2017). "Risks of unregulated use of alpha-melanocyte-stimulating hormone analogues: a review". International Journal of Dermatology. 56 (10): 975–980. doi:10.1111/ijd.13585. PMID 28266027. S2CID 37255702.