- Adrenorphin
-
Adrenorphin 
L-tyrosylglycylglycyl-L-phenylalanyl-L-methionyl-N~5~-(diaminomethylidene)-L-ornithyl-N~5~-(diaminomethylidene)-D-ornithyl-L-valinamideIdentifiers CAS number 88377-68-8 
PubChem 122176 ChemSpider 108968 Jmol-3D images Image 1 - O=C(N)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)Cc2ccccc2)CCSC)CCC/N=C(\N)N)CCC/N=C(\N)N)C(C)C
- InChI=1S/C44H69N15O9S/c1-25(2)36(37(46)63)59-41(67)31(12-8-19-52-44(49)50)57-39(65)30(11-7-18-51-43(47)48)56-40(66)32(17-20-69-3)58-42(68)33(22-26-9-5-4-6-10-26)55-35(62)24-53-34(61)23-54-38(64)29(45)21-27-13-15-28(60)16-14-27/h4-6,9-10,13-16,25,29-33,36,60H,7-8,11-12,17-24,45H2,1-3H3,(H2,46,63)(H,53,61)(H,54,64)(H,55,62)(H,56,66)(H,57,65)(H,58,68)(H,59,67)(H4,47,48,51)(H4,49,50,52)/t29-,30-,31+,32-,33-,36-/m0/s1
Key: XJOQRTJDYAHKPY-YVWIMRNGSA-N
InChI=1S/C44H69N15O9S/c1-25(2)36(37(46)63)59-41(67)31(12-8-19-52-44(49)50)57-39(65)30(11-7-18-51-43(47)48)56-40(66)32(17-20-69-3)58-42(68)33(22-26-9-5-4-6-10-26)55-35(62)24-53-34(61)23-54-38(64)29(45)21-27-13-15-28(60)16-14-27/h4-6,9-10,13-16,25,29-33,36,60H,7-8,11-12,17-24,45H2,1-3H3,(H2,46,63)(H,53,61)(H,54,64)(H,55,62)(H,56,66)(H,57,65)(H,58,68)(H,59,67)(H4,47,48,51)(H4,49,50,52)/t29-,30-,31+,32-,33-,36-/m0/s1
Key: XJOQRTJDYAHKPY-YVWIMRNGBT
InChI=1/C44H69N15O9S/c1-25(2)36(37(46)63)59-41(67)31(12-8-19-52-44(49)50)57-39(65)30(11-7-18-51-43(47)48)56-40(66)32(17-20-69-3)58-42(68)33(22-26-9-5-4-6-10-26)55-35(62)24-53-34(61)23-54-38(64)29(45)21-27-13-15-28(60)16-14-27/h4-6,9-10,13-16,25,29-33,36,60H,7-8,11-12,17-24,45H2,1-3H3,(H2,46,63)(H,53,61)(H,54,64)(H,55,62)(H,56,66)(H,57,65)(H,58,68)(H,59,67)(H4,47,48,51)(H4,49,50,52)/t29-,30-,31+,32-,33-,36-/m0/s1
Key: XJOQRTJDYAHKPY-YVWIMRNGBT
Properties Molecular formula C44H69N15O9S Molar mass 984.18 g/mol 
(verify) (what is: 
/
?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)Infobox references Adrenorphin, also sometimes referred to as metorphamide, is an endogenous, C-terminally amidated, opioid octapeptide (Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-NH2) that is produced from proteolyic cleavage of proenkephalin A and is widely distributed throughout the mammalian brain.[1][2][3][4][5] It was named based on the fact that it was originally detected in human phaeochromocytoma tumour derived from the adrenal medulla, and was subsequently found in normal human and bovine adrenal medulla as well.[1] Adrenorphin exhibits potent opioid activity, acting as a balanced μ- and κ-opioid receptor agonist, while having no effects on δ-opioid receptors.[2] It has analgesic and respiratory depressant effects.[6]
See also
References
- ^ a b Matsuo H, Miyata A, Mizuno K (1983). "Novel C-terminally amidated opioid peptide in human phaeochromocytoma tumour". Nature 305 (5936): 721–3. doi:10.1038/305721a0. PMID 6633641.
- ^ a b Weber E, Esch FS, Böhlen P et al. (December 1983). "Metorphamide: isolation, structure, and biologic activity of an amidated opioid octapeptide from bovine brain". Proceedings of the National Academy of Sciences of the United States of America 80 (23): 7362–6. doi:10.1073/pnas.80.23.7362. PMC 390055. PMID 6316361. http://www.pnas.org/cgi/pmidlookup?view=long&pmid=6316361.
- ^ Sonders M, Barchas JD, Weber E (August 1984). "Regional distribution of metorphamide in rat and guinea pig brain". Biochemical and Biophysical Research Communications 122 (3): 892–8. doi:10.1016/0006-291X(84)91174-4. PMID 6477570. http://linkinghub.elsevier.com/retrieve/pii/0006-291X(84)91174-4.
- ^ Miyata A, Mizuno K, Minamino N, Matsuo H (May 1984). "Regional distribution of adrenorphin in rat brain: comparative study with PH-8P". Biochemical and Biophysical Research Communications 120 (3): 1030–6. doi:10.1016/S0006-291X(84)80210-7. PMID 6732783. http://linkinghub.elsevier.com/retrieve/pii/S0006-291X(84)80210-7.
- ^ Miyata A, Mizuno K, Honzawa M, Tohyama M, Matsuo H (February 1985). "Adrenorphin immunoreactivity in rat brain". Neuropeptides 5 (4–6): 517–20. doi:10.1016/0143-4179(85)90068-X. PMID 2860609. http://linkinghub.elsevier.com/retrieve/pii/0143-4179(85)90068-X.
- ^ Xu SF, Lu WX, Zhou KR et al. (April 1985). "The analgesic and respiratory depressant actions of metorphamide in mice and rabbits". Neuropeptides 6 (2): 121–31. doi:10.1016/0143-4179(85)90103-9. PMID 4000426.
Peptides: neuropeptides Hormones see hormonesOpioid peptides Beta-endorphin • Alpha-endorphin • Gamma-endorphin • α-neo-endorphin • β-neo-endorphinOthersOther neuropeptides NeuromedinsOtherAngiotensin · Bombesin · Calcitonin gene-related peptide · Carnosine · Cocaine and amphetamine regulated transcript · Delta sleep-inducing peptide · FMRFamide · Galanin · Galanin-like peptide · Gastrin releasing peptide · Neuropeptide S · Neuropeptide Y · Neurophysins · Neurotensin · Pancreatic polypeptide · Pituitary adenylate cyclase activating peptide · RVD-Hpα · VGFB trdu: iter (nrpl/grfl/cytl/horl), csrc (lgic, enzr, gprc, igsr, intg, nrpr/grfr/cytr), itra (adap, gbpr, mapk), calc, lipd; path (hedp, wntp, tgfp+mapp, notp, jakp, fsap, hipp, tlrp) Opioids Opium and
poppy straw
derivativesCrude opiate extracts/
whole opium productsCompote/Kompot/Polish heroin • Diascordium • B & O Supprettes • Dover's powder • Kendal Black Drop • Laudanum • Mithridate • Opium • Paregoric • Poppy straw concentrate • Poppy tea • Smoking opium • Theriac
Natural opiates Opium alkaloids
see also: Components of opiumAlkaloid salts mixtures Semisynthetics
including
Bentley compoundsMorphine family 3,6-diesters of morphine Acetylpropionylmorphine • Diacetyldihydromorphine (Dihydroheroin, Acetylmorphinol) • Dibenzoylmorphine • Dipropanoylmorphine • Heroin (Diacetylmorphine) • Nicomorphine
Codeine-dionine family Morphinones and morphols 14-Cinnamoyloxycodeinone • 14-Ethoxymetopon • 14-Methoxymetopon • 14-Phenylpropoxymetopon • 7-Spiroindanyloxymorphone • Acetylmorphone • Codeinone • Codorphone • Codoxime • Thebacon (Acetyldihydrocodeinone / Dihydrocodeinone enol acetate) • Hydrocodone • Hydromorphone • Metopon • Morphinone • N-Phenethyl-14-ethoxymetopon • Oxycodone • Oxymorphol • Oxymorphone • Pentamorphone • Semorphone
Morphides Dihydrocodeine series 14-hydroxydihydrocodeine • Acetyldihydrocodeine • Dihydrocodeine • Nicocodeine • Nicodicodeine
Hydrazones Halogenated morphine derivatives 1-Iodomorphine
Active opiate
metabolitesMorphine-6-glucuronide • 6-Monoacetylmorphine • Norcodeine • Normorphine
Morphinans Morphinan series Cyclorphan • Dextrallorphan • Levorphanol • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Methorphan / Racemethorphan • Morphanol / Racemorphanol • Ro4-1539 • Xorphanol
Others Benzomorphans 8-Carboxamidocyclazocine • Alazocine • Bremazocine • Dezocine • Ketazocine • Metazocine • Pentazocine • Phenazocine
4-Phenylpiperidines Pethidines
(Meperidines)4-Fluoromeperidine • Allylnorpethidine • Anileridine • Benzethidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine (Carbetidine) • Furethidine • Hydroxypethidine (Bemidone) • Morpheridine • Oxpheneridine (Carbamethidine) • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Pheneridine • Phenoperidine • Piminodine • Properidine (Ipropethidine) • Sameridine
Prodines Ketobemidones Others Open chain
opioidsAmidones Methadols Moramides Dextromoramide • Levomoramide • Racemoramide
Thiambutenes Phenalkoxams Ampromides Others IC-26 • Isoaminile • Lefetamine • R-4066
Anilidopiperidines 3-Allylfentanyl • 3-Methylfentanyl • 3-Methylthiofentanyl • 4-Phenylfentanyl • Alfentanil • α-methylacetylfentanyl • α-methylfentanyl • α-methylthiofentanyl • β-hydroxyfentanyl • β-hydroxythiofentanyl • β-methylfentanyl • Brifentanil • Carfentanil • Fentanyl • Lofentanil • Mirfentanil • Ocfentanil • Ohmefentanyl • Parafluorofentanyl • Phenaridine • Remifentanil • Sufentanil • Thiofentanyl • Trefentanil
Oripavine
derivativesPhenazepanes Pirinitramides Benzimidazoles Indoles Diphenylmethylpiperazines Opioid peptides
see also: Opioid neuropeptidesAdrenorphin • Amidorphin • Casomorphin • DADLE • DAMGO • Dermorphin • Dynorphin • Endomorphin • Endorphins • Enkephalin • Gliadorphin • Morphiceptin • Nociceptin • Octreotide • Opiorphin • Rubiscolin • TRIMU 5
Others AD-1211 • AH-7921 • Azaprocin • BDPC • BRL-52537 • Bromadoline • C-8813 • Ciramadol • Doxpicomine • Enadoline • Faxeladol • GR-89696 • Herkinorin • ICI-199,441 • ICI-204,448 • J-113,397 • JTC-801 • Ketamine • LPK-26 • Methopholine • MT-45 • N-Desmethylclozapine • NNC 63-0532 • Nortilidine • O-Desmethyltramadol • Phencyclidine • Prodilidine • Profadol • Ro64-6198 • Salvinorin A • SB-612,111 • SC-17599 • RWJ-394,674 • TAN-67 • Tapentadol • Tifluadom • Tilidine • Tramadol • Trimebutine • U-50,488 • U-69,593 • Viminol • W-18
Opioid antagonists
&
inverse agonists5'-Guanidinonaltrindole • Alvimopan • Chlornaltrexamine • Cyclazocine • Cyprodime • Diprenorphine (M5050) • JDTic • Levallorphan • Methylnaltrexone • Nalfurafine • Nalmefene • Naloxazone • Naloxonazine • Naloxone • Nalorphine • Naltrexone • Naltriben • Naltrindole • Norbinaltorphimine • Oxilorphan
List of opioids Categories:- Analgesics
- Neurotransmitters
- Opioids
- Mu-opioid agonists
- Kappa agonists
- Peptides
Wikimedia Foundation. 2010.
