Melanotan II

Base Information

• Chemical Name: Melanotan II
• CAS No.: 121062-08-6
• Molecular Formula: C50H69N15O9
• Molecular Weight: 1024.19
• Hs Code.: 3504009000
• UNII: UPF5CJ93X7
• DSSTox Substance ID: DTXSID90153135
• Nikkaji Number: J1.279.156I
• Wikipedia: Melanotan_II
• Wikidata: Q423855
• ChEMBL ID: CHEMBL430239
• Mol file: 121062-08-6.mol

Synonyms:L-Lysinamide,N-acetyl-L-norleucyl-L-a-aspartyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophyl-, cyclic (2?;1,4,7,10,13,18-Hexaazacyclotricosane, cyclic peptide deriv.;17: PN:WO2006012667 PAGE: 40 claimed protein;19: PN: WO2008025074 SEQID: 19 claimedprotein;1: PN: WO2009033712PAGE: 103 claimed protein;2: PN: WO2006060873 SEQID: 2 claimed protein;MT II;PT 14;Melanotan-II;

Chemical Property of Melanotan II

Chemical Property:

• Appearance/Colour: solid
• Refractive Index: 1.669
• PKA: 13.00±0.70(Predicted)
• PSA: 382.26000
• Density: 1.43 g/cm³
• LogP: 3.60720
• Storage Temp.: −20°C
• Solubility.: H2O: 5 mg/mL, soluble
• XLogP3: 0
• Hydrogen Bond Donor Count: 13
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 17
• Exact Mass: 1023.54026884
• Heavy Atom Count: 74
• Complexity: 1950

Purity/Quality:

99.9% ^*data from raw suppliers

MT2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(C(=O)NC1CC(=O)NCCCCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CC2=CN=CN2)CC3=CC=CC=C3)CCCN=C(N)N)CC4=CNC5=CC=CC=C54)C(=O)N)NC(=O)C
• Isomeric SMILES: 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
• Description: Melanotan II is a synthetic analogue of the melanocortin peptide hormone alpha-melanocyte stimulating hormone (α-MSH) that occurs naturally. In usage, Melanotan II has been revealed to have aphrodisiac and melanogenesis (tanning) effects that have been subjected to clinical trials and preliminary studies. The compound is a cyclic lactam analogue of α-MSH that has an amino sequence named MTII (Ac-Nle-c[Asp-His-D-Phe-Arg-Trp-Lys]-NH2). Notably, no government drug regulatory agency across the world had approved for the use of any compound incorporating the Melanotan II peptide by 2010
• Uses: Malanotan II is used for tanning of the skin and producing of erections in men with erectile dysfunction when administered as a shot under the skin. Malanotan II is safe when used under strict medical supervision for treating erectile dysfunction. However, it may cause stomach cramps, tiredness, nausea, spontaneous erections of the penis, and darkened skin. Melanotan II acetate salt has been used to study its inhibitory effects on feeding and energy expenditure in rats. Melanotan II Acetic Acid Salt, is a lab-made chemical that is similar to a hormone found in people. Melanotan II has been shown to have melanogenesis (tanning) and aphrodisiac effects on humans.
• Clinical Use: Melanotan II has been a new treatment for rosacea discussed in the various rosacea support groups on the internet. Melanotan I and Melanotan II are both analogs of the peptide hormone alpha-melanocyte stimulating hormone (a-MSH) that tend to induce skin tanning. Melanotan II has the additional effect of increasing libido. Melanotan II is an α-MSH analog which underwent clinical trials for the treatment of erectile dysfunction. Preliminary double-blind, placebo-controlled studies demonstrated the efficacy of melanotan in inducing penile erection in men with erectile dysfunction, although in a very restricted population.Unfortunately, there are no experimental data on the mode of action of melanotan II, as melanotan II is the first α-MSH agonist inducing penile erection when injected peripherally. Illustration of the proerectile effect of melanotan II (MT-II) in humans. Placebo (A) or MT-II (B, 25 ug/kg and C, 133 ug/kg) was injected subcutaneously in patients and RigiScan recording was performed from 6 h. Apparent erections developed in 8 of 10 men treated with MT-II. (Reproduced with permission from Wessells H et al. Effect of an alphamelanocyte stimulating hormone analog on penile erection and sexual desire in men with organic erectile dysfunction. Urology 2000; 56:641–646.)

Technology Process of Melanotan II

There total 5 articles about Melanotan II which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 30.0%

Ac-Nle-Asp-His-D-Phe-Arg-Trp-Lys-NH2 (117499-53-3) → melanotan-II (121062-08-6)

Guidance literature:

With dipotassium hydrogenphosphate; diphenyl phosphoryl azide; In N,N-dimethyl-formamide; 1) 0 deg C, 6 h, 2) r.t., overnight;

DOI:10.1021/jm00132a010

Reference yield:

C94H103N14O14PolS + acetic anhydride (108-24-7) + Fmoc-(S)-2-aminohexanoic acid (77284-32-3,144701-20-2) → melanotan-II (121062-08-6)

Guidance literature:

C₉₄H₁₀₃N₁₄O₁₄PolS; With piperidine; benzotriazol-1-ol; In dichloromethane; N,N-dimethyl-d₆-formamide; at 20 - 75 ℃; for 0.1h; rink-amide-MBHA resin Microwave irradiation;

Fmoc-(S)-2-aminohexanoic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 75 ℃; for 0.0833333h; rink-amide-MBHA resin Microwave irradiation;

acetic anhydride; Further stages;

DOI:10.1016/j.bmcl.2015.10.095

Reference yield:

Boc-Arg(Tos)-OH (13836-37-8) + Boc-Lys(Fmoc)-OH (84624-27-1) + Boc-D-Phe-OH (18942-49-9) + Nα-tert-butoxycarbonyl-1-formyl-L-tryptophan (47355-10-2) → melanotan-II (121062-08-6)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1021/jm00132a010

upstream raw materials:

Ac-Nle-Asp-His-D-Phe-Arg-Trp-Lys-NH₂

Boc-Arg(Tos)-OH

Boc-Lys(Fmoc)-OH

Boc-D-Phe-OH

Refernces

• 1、 Haskell-Luevano, Carrie,Toth, Kate,Boteju, Lakmal,Job, Constatin,Castrucci, Ana Maria De L.,Hadley, Mac E.,Hruby, Victor J.. "β-methylation of the Phe7 and Trp9 melanotropin side chain pharmacophores affects ligand-receptor interactions and prolonged biological activity". . p. 2740 - 2749. Retrieved 1997.
• 2、 Al-Obeidi, Fahad,Castrucci, Ana M. de L.,Hadley, Mac E.,Hruby, Victor J.. "Potent and Prolonged Acting Cyclic Lactam Analogues of α-Melanotropin: Design Based on Molecular Dynamics". . p. 2555 - 2561. Retrieved 2007/10/02.