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121062-08-6,MFCD01318793
Catalog No.:AA01DQ73

121062-08-6 | Melanotan II

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2mg
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5mg
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10mg
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25mg
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50mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA01DQ73
Chemical Name:
Melanotan II
CAS Number:
121062-08-6
Molecular Formula:
C50H69N15O9
Molecular Weight:
1024.1780
MDL Number:
MFCD01318793
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)Cc1nc[nH]c1)Cc1ccccc1)CCCNC(=N)N)Cc1c[nH]c2c1cccc2)C(=O)N)NC(=O)C
Properties
Computed Properties
 
Complexity:
1950  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
7  
Heavy Atom Count:
74  
Hydrogen Bond Acceptor Count:
11  
Hydrogen Bond Donor Count:
13  
Rotatable Bond Count:
17  

Literature

Title: The melanocortin-4 receptor as target for obesity treatment: a systematic review of emerging pharmacological therapeutic options.

Journal: International journal of obesity (2005) 20140201

Title: Food intake reductions and increases in energetic responses by hindbrain leptin and melanotan II are enhanced in mice with POMC-specific PTP1B deficiency.

Journal: American journal of physiology. Endocrinology and metabolism 20120901

Title: Melanocortin receptor 4 deficiency affects body weight regulation, grooming behavior, and substrate preference in the rat.

Journal: Obesity (Silver Spring, Md.) 20120301

Title: Anatomical dissociation of melanocortin receptor agonist effects on taste- and gut-sensitive feeding processes.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20111001

Title: Assessment of voluntary ethanol consumption and the effects of a melanocortin (MC) receptor agonist on ethanol intake in mutant C57BL/6J mice lacking the MC-4 receptor.

Journal: Alcoholism, clinical and experimental research 20110601

Title: Systemic but not central nervous system nitric oxide synthase inhibition exacerbates the hypertensive effects of chronic melanocortin-3/4 receptor activation.

Journal: Hypertension (Dallas, Tex. : 1979) 20110301

Title: Activation of the melanocortin-4 receptor causes enhanced excitation in presympathetic paraventricular neurons in obese Zucker rats.

Journal: Regulatory peptides 20110117

Title: Central melanocortin stimulation increases phosphorylated perilipin A and hormone-sensitive lipase in adipose tissues.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20100701

Title: Melanocortin activity in the amygdala controls appetite for dietary fat.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20100201

Title: Distinct effects of leptin and a melanocortin receptor agonist injected into medial hypothalamic nuclei on glucose uptake in peripheral tissues.

Journal: Diabetes 20091201

Title: Melanocortins may stimulate reproduction by activating orexin neurons in the dorsomedial hypothalamus and kisspeptin neurons in the preoptic area of the ewe.

Journal: Endocrinology 20091201

Title: Substitution of arginine with proline and proline derivatives in melanocyte-stimulating hormones leads to selectivity for human melanocortin 4 receptor.

Journal: Journal of medicinal chemistry 20090625

Title: Melanocortin-4 receptor mRNA expressed in sympathetic outflow neurons to brown adipose tissue: neuroanatomical and functional evidence.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20080801

Title: Reflex penile erection in anesthetized mice: an exploratory study.

Journal: Neuroscience 20080731

Title: 5-HT(2C) receptor activation is a common mechanism on proerectile effects of apomorphine, oxytocin and melanotan-II in rats.

Journal: European journal of pharmacology 20080728

Title: Presynaptic melanocortin-4 receptors on vagal afferent fibers modulate the excitability of rat nucleus tractus solitarius neurons.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20080507

Title: Structure-activity relationships of cyclic lactam analogues of alpha-melanocyte-stimulating hormone (alpha-MSH) targeting the human melanocortin-3 receptor.

Journal: Journal of medicinal chemistry 20080124

Title: Functional evaluation of THIQ, a melanocortin 4 receptor agonist, in models of food intake and inflammation.

Journal: Basic & clinical pharmacology & toxicology 20071201

Title: Differential activation of the sympathetic innervation of adipose tissues by melanocortin receptor stimulation.

Journal: Endocrinology 20071101

Title: Melanocortins and agouti-related protein modulate the excitability of two arcuate nucleus neuron populations by alteration of resting potassium conductances.

Journal: The Journal of physiology 20070115

Title: A liquid chromatographic/tandem mass spectroscopic method for quantification of the cyclic peptide melanotan-II. Plasma and brain tissue concentrations following administration in mice.

Journal: Rapid communications in mass spectrometry : RCM 20070101

Title: Design, synthesis, and biological evaluation of new cyclic melanotropin peptide analogues selective for the human melanocortin-4 receptor.

Journal: Journal of medicinal chemistry 20061116

Title: The melanocortin agonist, melanotan II, enhances proceptive sexual behaviors in the female rat.

Journal: Pharmacology, biochemistry, and behavior 20061101

Title: Cell signaling and trafficking of human melanocortin receptors in real time using two-photon fluorescence and confocal laser microscopy: differentiation of agonists and antagonists.

Journal: Chemical biology & drug design 20061001

Title: Development of cyclic gamma-MSH analogues with selective hMC3R agonist and hMC3R/hMC5R antagonist activities.

Journal: Journal of medicinal chemistry 20060323

Title: Reduced anorexigenic efficacy of leptin, but not of the melanocortin receptor agonist melanotan-II, predicts diet-induced obesity in rats.

Journal: Endocrinology 20051201

Title: Intracerebroventricular administration of melanotan II increases insulin sensitivity of glucose disposal in mice.

Journal: Diabetologia 20050801

Title: Effects of melanocortin receptor activation and blockade on ethanol intake: a possible role for the melanocortin-4 receptor.

Journal: Alcoholism, clinical and experimental research 20050601

Title: Pharmacotherapy for erectile dysfunction.

Journal: The journal of sexual medicine 20040901

Title: The melanocortin agonist melanotan II increases insulin sensitivity in OLETF rats.

Journal: Peptides 20040801

Title: Unabated anorexic and enhanced thermogenic responses to melanotan II in diet-induced obese rats despite reduced melanocortin 3 and 4 receptor expression.

Journal: The Journal of endocrinology 20040701

Title: Adrenalectomy alters the sensitivity of the central nervous system melanocortin system.

Journal: Diabetes 20031201

Title: MTII-induced reduction of voluntary ethanol drinking is blocked by pretreatment with AgRP-(83-132).

Journal: Neuropeptides 20031201

Title: Extensive structure-activity studies of lactam derivatives of MT-II and SHU-9119: their activity and selectivity at human melanocortin receptors 3, 4, and 5.

Journal: The journal of peptide research : official journal of the American Peptide Society 20031101

Title: Structure-activity relationship of cyclic peptide penta-c[Asp-His(6)-DPhe(7)-Arg(8)-Trp(9)-Lys]-NH(2) at the human melanocortin-1 and -4 receptors: His(6) substitution.

Journal: Bioorganic & medicinal chemistry letters 20030407

Title: Structure-activity relationships of the melanocortin tetrapeptide Ac-His-D-Phe-Arg-Trp-NH2 at the mouse melanocortin receptors. 4. Modifications at the Trp position.

Journal: Journal of medicinal chemistry 20021219

Title: Structure-activity relationships of the melanocortin tetrapeptide Ac-His-DPhe-Arg-Trp-NH(2) at the mouse melanocortin receptors: part 2 modifications at the Phe position.

Journal: Journal of medicinal chemistry 20020704

Title: The leptin-like effects of 3-d peripheral administration of a melanocortin agonist are more marked in genetically obese Zucker (fa/fa) than in lean rats.

Journal: Endocrinology 20020601

Title: [New medications for treatment of erectile dysfunction].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20020601

Title: The role of melanocortins in body weight regulation: opportunities for the treatment of obesity.

Journal: European journal of pharmacology 20020412

Title: Activation of central melanocortin receptors by MT-II increases cavernosal pressure in rabbits by the neuronal release of NO.

Journal: British journal of pharmacology 20011201

Title: Molecular determinants of ligand binding to the human melanocortin-4 receptor.

Journal: Biochemistry 20001205

Title: Characterization of melanocortin receptor ligands on cloned brain melanocortin receptors and on grooming behavior in the rat.

Journal: European journal of pharmacology 19990813

Title: Evaluation of melanotan-II, a superpotent cyclic melanotropic peptide in a pilot phase-I clinical study.

Journal: Life sciences 19960101

Title: Topographical modification of melanotropin peptide analogues with beta-methyltryptophan isomers at position 9 leads to differential potencies and prolonged biological activities.

Journal: Journal of medicinal chemistry 19951110

Title: Design of potent linear alpha-melanotropin 4-10 analogues modified in positions 5 and 10.

Journal: Journal of medicinal chemistry 19890101

Title: Breindahl T, et al. Identification and characterization by LC-UV-MS/MS of melanotan II skin-tanning products sold illegally on the Internet. Drug Test Anal. 2015 Feb;7(2):164-72.

Title: Giuliano F, et al. Melanotan-II: Investigation of the inducer and facilitator effects on penile erection in anaesthetized rat. Neuroscience. 2006;138(1):293-301.

Title: Ter Laak MP, et al. The potent melanocortin receptor agonist melanotan-II promotes peripheral nerve regeneration and has neuroprotective properties in the rat. Eur J Pharmacol. 2003 Feb 21;462(1-3):179-83.

Title: Wessells H, et al. Melanocortin receptor agonists, penile erection, and sexual motivation: human studies with Melanotan II. Int J Impot Res. 2000 Oct;12 Suppl 4:S74-9.

Title: De Jonghe BC, et al. Food intake reductions and increases in energetic responses by hindbrain leptin and melanotan II are enhanced in mice with POMC-specific PTP1B deficiency. Am J Physiol Endocrinol Metab. 2012 Sep 1;303(5):E644-51.

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