Melanotan II
Properties
| Molecular Formula | C50H69N15O9 |
|---|---|
| Molecular Weight | 1024.2 |
| Monoisotopic Mass | 1023.54026884 |
| Polar Area | 385 |
| Complexity | 1950 |
| XLogP | 0 |
| Heavy Atom Count | 74 |
| Hydrogen Bond Donor Count | 13 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 17 |
| Physical Appearance | Fine White Lyophilized Powder |
| Stability | Lyophilized protein is to be stored at -20°C. It is recommended to aliquot the reconstituted (dissolved) protein into several discrete vials in order to avoid repeated freezing and thawing. Reconstituted protein can be stored at 4°C |
| PubChem LCSS |
Identifiers
| CID | 92432 |
|---|---|
| CAS | 121062-08-6 |
| 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 |
| InChIKey | JDKLPDJLXHXHNV-MFVUMRCOSA-N |
| 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 |
| 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 |
| IUPAC Name | (3S, 6S, 9R, 12S, 15S, 23S)-15-[[(2S)-2-acetamidohexanoyl]amino]-9-benzyl-6-[3-(diaminomethylideneamino)propyl]-12-(1H-imidazol-5-ylmethyl)-3-(1H-indol-3-ylmethyl)-2, 5, 8, 11, 14, 17-hexaoxo-1, 4, 7, 10, 13, 18-hexazacyclotricosane-23-carboxamide |
Description
Melanotan II
Product is sold for prescriber purposes only. Please handle with care and follow all safety guidelines for the specific chemicals involved.
Melanotan II (MT-II), a synthetic analog of α-melanocyte-stimulating hormone, is a potent non-selective agonist of melanocortin receptors (MCRs). In rat models, MT-II has been extensively studied for its effects on energy homeostasis, feeding behavior, thermoregulation, and neuroendocrine functions.
One of the primary applications of MT-II in rodent research is its anorexigenic effect. Central administration of MT-II significantly reduces food intake and body weight in rats, implicating the melanocortin-3 and -4 receptors (MC3R and MC4R) in the regulation of appetite and energy balance. These effects are observed when MT-II is administered into various brain regions, including the forebrain and hindbrain ventricles, suggesting a distributed control of feeding behavior via MCRs.
Additionally, MT-II has been shown to influence thermoregulation. Peripheral administration of MT-II induces hypothermia in mice by activating mast cells and stimulating histamine receptors, indicating a mechanism independent of the canonical melanocortin receptors. This finding highlights the complex interplay between MT-II and various physiological systems beyond the central nervous system.
MT-II also affects sexual behavior in rodents. Studies have shown that MT-II enhances proceptive sexual behaviors in female rats, indicating its influence on sexual motivation and behavior through central melanocortin pathways.
Moreover, MT-II has been implicated in modulating reward-related behaviors. Microinjection of MT-II into the nucleus accumbens of rats reduced motivation to obtain food without affecting actual food intake, suggesting a role in the regulation of appetitive behaviors.
In summary, MT-II serves as a valuable tool in rodent research for investigating the melanocortin system’s role in various physiological and behavioral processes. Its multifaceted effects on feeding, thermoregulation, neural recovery, sexual behavior, and motivation underscore its significance in preclinical studies.
References:
- Raposinho, P. D., White, R. B., & Aubert, M. L. (2003). The melanocortin agonist melanotan-II reduces the orexigenic and adipogenic effects of neuropeptide Y (NPY) but does not affect the NPY-driven suppressive effects on the gonadotropic and somatotropic axes in the male rat. Journal of Neuroendocrinology, 15(2), 173–181.
- Jain, S., Panyutin, A., Liu, N., Xiao, C., Pinol, R. A., & Pundir, P. (2018). Melanotan II causes hypothermia in mice by activation of mast cells and stimulation of histamine 1 receptors. American Journal of Physiology-Endocrinology and Metabolism, 315(2), E357–E366.
- The potent melanocortin receptor agonist melanotan-II promotes recovery of sensory function following sciatic nerve injury in rats. European Journal of Pharmacology, 2002.
- The melanocortin agonist, melanotan II, enhances proceptive sexual behaviors in the female rat. Pharmacology Biochemistry and Behavior, 2006.
- Melanocortin receptor agonist melanotan-II microinjected in the nucleus accumbens reduces motivation to obtain food in rats. Physiology & Behavior, 2022.
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