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121062-08-6

Basic Information
CAS No.: 121062-08-6
Name: Melanotan II
Article Data: 4
Molecular Structure:
Molecular Structure of 121062-08-6 (Melanotan II)
Formula: C50H69N15O9
Molecular Weight: 1024.19
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;
EINECS: 1308068-626-2
Density: 1.43 g/cm3
Solubility: 5 mg/mL, soluble in water
Appearance: solid
Hazard Symbols: Xn
Risk Codes: 22
PSA: 382.26000
LogP: 3.60720
Synthetic route

121062-08-6

melanotan-II

13836-37-8

Boc-Arg(Tos)-OH

84624-27-1

Boc-Lys(Fmoc)-OH

18942-49-9

Boc-D-Phe-OH

47355-10-2

Nα-tert-butoxycarbonyl-1-formyl-L-tryptophan

Nα-Boc-His(Nϖ-Bom), Nα-Boc-Asp(β-Fmo), Nα-Boc-Nle, Ac2O

Nα-Boc-His(Nϖ-Bom), Nα-Boc-Asp(β-Fmo), Nα-Boc-Nle, Ac2O

121062-08-6

melanotan-II

Conditions
ConditionsYield
Yield given. Multistep reaction;
13836-37-8

Boc-Arg(Tos)-OH

84624-27-1

Boc-Lys(Fmoc)-OH

18942-49-9

Boc-D-Phe-OH

92916-47-7

Nα-Boc-Trp (Nin-MeS)

Nα-Boc-His (Nϖ-Bom), Nα-Boc-Asp (β-OFm), Nα-Boc-Nle, Ac2O

Nα-Boc-His (Nϖ-Bom), Nα-Boc-Asp (β-OFm), Nα-Boc-Nle, Ac2O

121062-08-6

melanotan-II

Conditions
ConditionsYield
Multistep reaction;
269066-08-2

Fmoc-Asp(ODmab)-OH; Dmab = 4-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino}benzyl

108-24-7

acetic anhydride

86123-10-6

Fmoc-D-Phe-OH

109425-51-6

Fmoc-His(Trt)-OH

77284-32-3

Fmoc-(S)-2-aminohexanoic acid

150629-67-7

Fmoc-Lys(Dde)-OH

143824-78-6

3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine

121062-08-6

melanotan-II

Conditions
ConditionsYield
Stage #1: Fmoc-Lys(Dde)-OH With 4-methyl-morpholine; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide for 0.666667h;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.416667h;
Stage #3: Fmoc-Asp(ODmab)-OH; Dmab = 4-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino}benzyl; acetic anhydride; Fmoc-D-Phe-OH; Fmoc-His(Trt)-OH; Fmoc-(S)-2-aminohexanoic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;

C94H103N14O14PolS

108-24-7

acetic anhydride

77284-32-3

Fmoc-(S)-2-aminohexanoic acid

121062-08-6

melanotan-II

Conditions
ConditionsYield
Stage #1: 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;
Stage #2: 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;
Stage #3: acetic anhydride Further stages;
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    Name:Melanotan II Alias: α -melanocyte promoting hormone (MT-II); Meranotan acetate; The melanin; Melanin ⅱ acetate; Menoratan-2 English Name:Melanotan II English aliases:AC-NLE-CYCLO(-BETA-ASP-HIS-D-PHE-ARG-TRP-EPSILON-LYS-NH2) CAS No.1210

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History

 Melanotan II (CAS NO.121062-08-6) was first synthesized at the University of Arizona. Researchers decided to find a more potent and stable alternative, one that would be more practical to defenses against skin cancer.
The researchers headed by Victor Hruby, found a peptide, [Nle4, D-Phe7]-α-MSH, that was approximately 1,000 times more potent than natural α-MSH after synthesizing and screening hundreds of molecules. They dubbed this new peptide, "Melanotan" (later Melanotan I, now known as afamelanotide). They subsequently developed another analog, Ac-Nle-cyclo[Asp-His-D-Phe-Arg-Trp-Lys]-NH2), which they named "Melanotan ⅡAcetate". Since their discovery, numerous studies dating back to the mid-1980s have found no obvious toxic effects of the Melanotan peptides. The scientists hoped to use Melanotan peptides to combat melanoma by stimulating the body's natural tanning mechanism to create a tan without first needing exposure to harmful levels of UV radiation. This in turn, they hypothesized, could reduce the potential for skin damage that can eventually lead to skin cancer.
The scientists licensed their patented peptides, via a technology transfer company, to a number of biotechnology companies who intend to develop them into drugs.

Specification

The Melanotan II, with the CAS registry number 121062-08-6.It belongs to the product Pharmaceutical Intermediates. This chemical's molecular formula is C50H69N15O9 and molecular weight is 1024.17.What's more,Its systematic name is L-Lysinamide,N-acetyl-L-norleucyl-L-alpha-aspartyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophyl-,cyclic (2-7)-peptide. The Melanotan II with the capable of stimulating melanin synthesis & promoting rapid tanning of skin.Currently it is in trials for use in the prevention of sunlight-induced skin cancer. 

Physical properties about Melanotan II are: (1)Density: 1.43 g/cm3 ; (2)Index of Refraction: 1.683 ; (3)Molar Refractivity: 269.94 cm3 ; (4)Molar Volume: 711.6 cm3 ; (5)Surface Tension: 63 dyne/cm ; (6)Storage Temp.: -20 °C; (7)Water Solubility: 5 mg/mL, soluble; (8)Form: solid; (9)H-Bond Donor: 13 ; (10)H-Bond Acceptor: 13 ; (11)Rotatable Bond Count: 17 ; (12)Tautomer Count: 1000 ; (13)Exact Mass: 1023.540269 ; (14)MonoIsotopic Mass: 1023.540269 ; (15)Topological Polar Surface Area: 385 ; (16)Heavy Atom Count: 74 ;

You can still convert the following datas into molecular structure:
(1)SMILES:O=C(N[C@H](C(=O)N[C@@H]1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CCCCNC(=O)C1)Cc3c2ccccc2nc3)CCC/N=C(\N)N)Cc4ccccc4)Cc5cncn5)CCCC)C;
(2)Std. InChI: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;
(3)Std. InChIKey:JDKLPDJLXHXHNV-MFVUMRCOSA-N.