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{{Chembox
{{Chembox
| verifiedrevid = 446609792
| verifiedrevid = 447369158
| ImageFile = Amidorphin.png
| ImageFile = Amidorphin.svg
| ImageSize = 200px
| ImageSize = 200px
| IUPACName =
| IUPACName =
| OtherNames =
| OtherNames =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 94885-44-6
| PubChem = 16132380
| CASNo = 94885-44-6
| PubChem = 16132380
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 17289039
| ChemSpiderID = 17289039
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C131H200N30O43S2/c1-66(2)54-88(110(136)183)153-130(203)109(70(9)10)159-122(195)80(35-41-101(169)170)142-99(167)64-137-98(166)63-140-113(186)92(60-96(135)164)154-111(184)71(11)141-114(187)81(36-42-102(171)172)146-117(190)82(37-43-103(173)174)147-118(191)84(39-45-105(177)178)152-129(202)108(69(7)8)160-123(196)85(40-46-106(179)180)149-124(197)90(56-68(5)6)157-128(201)95-26-21-51-161(95)131(204)94(59-74-29-33-76(163)34-30-74)158-125(198)89(55-67(3)4)155-119(192)83(38-44-104(175)176)148-127(200)93(61-107(181)182)156-121(194)87(48-53-206-13)150-116(189)79(25-18-20-50-133)144-115(188)78(24-17-19-49-132)145-120(193)86(47-52-205-12)151-126(199)91(58-72-22-15-14-16-23-72)143-100(168)65-138-97(165)62-139-112(185)77(134)57-73-27-31-75(162)32-28-73/h14-16,22-23,27-34,66-71,77-95,108-109,162-163H,17-21,24-26,35-65,132-134H2,1-13H3,(H2,135,164)(H2,136,183)(H,137,166)(H,138,165)(H,139,185)(H,140,186)(H,141,187)(H,142,167)(H,143,168)(H,144,188)(H,145,193)(H,146,190)(H,147,191)(H,148,200)(H,149,197)(H,150,189)(H,151,199)(H,152,202)(H,153,203)(H,154,184)(H,155,192)(H,156,194)(H,157,201)(H,158,198)(H,159,195)(H,160,196)(H,169,170)(H,171,172)(H,173,174)(H,175,176)(H,177,178)(H,179,180)(H,181,182)/t71-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,108-,109-/m0/s1
| StdInChI = 1S/C131H200N30O43S2/c1-66(2)54-88(110(136)183)153-130(203)109(70(9)10)159-122(195)80(35-41-101(169)170)142-99(167)64-137-98(166)63-140-113(186)92(60-96(135)164)154-111(184)71(11)141-114(187)81(36-42-102(171)172)146-117(190)82(37-43-103(173)174)147-118(191)84(39-45-105(177)178)152-129(202)108(69(7)8)160-123(196)85(40-46-106(179)180)149-124(197)90(56-68(5)6)157-128(201)95-26-21-51-161(95)131(204)94(59-74-29-33-76(163)34-30-74)158-125(198)89(55-67(3)4)155-119(192)83(38-44-104(175)176)148-127(200)93(61-107(181)182)156-121(194)87(48-53-206-13)150-116(189)79(25-18-20-50-133)144-115(188)78(24-17-19-49-132)145-120(193)86(47-52-205-12)151-126(199)91(58-72-22-15-14-16-23-72)143-100(168)65-138-97(165)62-139-112(185)77(134)57-73-27-31-75(162)32-28-73/h14-16,22-23,27-34,66-71,77-95,108-109,162-163H,17-21,24-26,35-65,132-134H2,1-13H3,(H2,135,164)(H2,136,183)(H,137,166)(H,138,165)(H,139,185)(H,140,186)(H,141,187)(H,142,167)(H,143,168)(H,144,188)(H,145,193)(H,146,190)(H,147,191)(H,148,200)(H,149,197)(H,150,189)(H,151,199)(H,152,202)(H,153,203)(H,154,184)(H,155,192)(H,156,194)(H,157,201)(H,158,198)(H,159,195)(H,160,196)(H,169,170)(H,171,172)(H,173,174)(H,175,176)(H,177,178)(H,179,180)(H,181,182)/t71-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,108-,109-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BRCPMMMERAGFCE-ZIFJQKEFSA-N
| StdInChIKey = BRCPMMMERAGFCE-ZIFJQKEFSA-N
| SMILES = CC(C)CC(C(=O)N)NC(=O)C(C(C)C)NC(=O)C(CCC(=O)O)NC(=O)CNC(=O)CNC(=O)C(CC(=O)N)NC(=O)C(C)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C1CCCN1C(=O)C(Cc2ccc(cc2)O)NC(=O)C(CC(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CC(=O)O)NC(=O)C(CCSC)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(CCSC)NC(=O)C(Cc3ccccc3)NC(=O)CNC(=O)CNC(=O)C(Cc4ccc(cc4)O)N
| SMILES = CC(C)CC(C(=O)N)NC(=O)C(C(C)C)NC(=O)C(CCC(=O)O)NC(=O)CNC(=O)CNC(=O)C(CC(=O)N)NC(=O)C(C)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C1CCCN1C(=O)C(Cc2ccc(cc2)O)NC(=O)C(CC(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CC(=O)O)NC(=O)C(CCSC)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(CCSC)NC(=O)C(Cc3ccccc3)NC(=O)CNC(=O)CNC(=O)C(Cc4ccc(cc4)O)N
| InChI = InChI=1S/C131H200N30O43S2/c1-66(2)54-88(110(136)183)153-130(203)109(70(9)10)159-122(195)80(35-41-101(169)170)142-99(167)64-137-98(166)63-140-113(186)92(60-96(135)164)154-111(184)71(11)141-114(187)81(36-42-102(171)172)146-117(190)82(37-43-103(173)174)147-118(191)84(39-45-105(177)178)152-129(202)108(69(7)8)160-123(196)85(40-46-106(179)180)149-124(197)90(56-68(5)6)157-128(201)95-26-21-51-161(95)131(204)94(59-74-29-33-76(163)34-30-74)158-125(198)89(55-67(3)4)155-119(192)83(38-44-104(175)176)148-127(200)93(61-107(181)182)156-121(194)87(48-53-206-13)150-116(189)79(25-18-20-50-133)144-115(188)78(24-17-19-49-132)145-120(193)86(47-52-205-12)151-126(199)91(58-72-22-15-14-16-23-72)143-100(168)65-138-97(165)62-139-112(185)77(134)57-73-27-31-75(162)32-28-73/h14-16,22-23,27-34,66-71,77-95,108-109,162-163H,17-21,24-26,35-65,132-134H2,1-13H3,(H2,135,164)(H2,136,183)(H,137,166)(H,138,165)(H,139,185)(H,140,186)(H,141,187)(H,142,167)(H,143,168)(H,144,188)(H,145,193)(H,146,190)(H,147,191)(H,148,200)(H,149,197)(H,150,189)(H,151,199)(H,152,202)(H,153,203)(H,154,184)(H,155,192)(H,156,194)(H,157,201)(H,158,198)(H,159,195)(H,160,196)(H,169,170)(H,171,172)(H,173,174)(H,175,176)(H,177,178)(H,179,180)(H,181,182)/t71-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,108-,109-/m0/s1
| InChI = InChI=1S/C131H200N30O43S2/c1-66(2)54-88(110(136)183)153-130(203)109(70(9)10)159-122(195)80(35-41-101(169)170)142-99(167)64-137-98(166)63-140-113(186)92(60-96(135)164)154-111(184)71(11)141-114(187)81(36-42-102(171)172)146-117(190)82(37-43-103(173)174)147-118(191)84(39-45-105(177)178)152-129(202)108(69(7)8)160-123(196)85(40-46-106(179)180)149-124(197)90(56-68(5)6)157-128(201)95-26-21-51-161(95)131(204)94(59-74-29-33-76(163)34-30-74)158-125(198)89(55-67(3)4)155-119(192)83(38-44-104(175)176)148-127(200)93(61-107(181)182)156-121(194)87(48-53-206-13)150-116(189)79(25-18-20-50-133)144-115(188)78(24-17-19-49-132)145-120(193)86(47-52-205-12)151-126(199)91(58-72-22-15-14-16-23-72)143-100(168)65-138-97(165)62-139-112(185)77(134)57-73-27-31-75(162)32-28-73/h14-16,22-23,27-34,66-71,77-95,108-109,162-163H,17-21,24-26,35-65,132-134H2,1-13H3,(H2,135,164)(H2,136,183)(H,137,166)(H,138,165)(H,139,185)(H,140,186)(H,141,187)(H,142,167)(H,143,168)(H,144,188)(H,145,193)(H,146,190)(H,147,191)(H,148,200)(H,149,197)(H,150,189)(H,151,199)(H,152,202)(H,153,203)(H,154,184)(H,155,192)(H,156,194)(H,157,201)(H,158,198)(H,159,195)(H,160,196)(H,169,170)(H,171,172)(H,173,174)(H,175,176)(H,177,178)(H,179,180)(H,181,182)/t71-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,108-,109-/m0/s1
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>131</sub>H<sub>200</sub>N<sub>30</sub>O<sub>43</sub>S<sub>2</sub>
| Formula = C<sub>131</sub>H<sub>200</sub>N<sub>30</sub>O<sub>43</sub>S<sub>2</sub>
| MolarMass = 2947.29 g/mol
| MolarMass = 2947.29 g/mol
| Appearance =
| Appearance =
| Density =
| Density =
| MeltingPt =
| MeltingPt =
| BoilingPt =
| BoilingPt =
| Solubility =
| Solubility =
}}
}}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition =
| AutoignitionPt =
}}
}}
}}
}}


'''Amidorphin''' is an [[endogenous]], [[C-terminus|C-terminally]] [[amide|amidated]], [[opioid]] [[peptide]] generated as a [[cleavage|cleavage product]] of [[proenkephalin A]] that is widely distributed in the [[mammalian]] [[brain]], with particularly high concentrations found in the [[adrenal medulla]], [[posterior pituitary]], and [[striatum]].<ref name="pmid3965972">{{cite journal | author = Seizinger BR | title = Isolation and structure of a novel C-terminally amidated opioid peptide, amidorphin, from bovine adrenal medulla | journal = Nature | volume = 313 | issue = 5997 | pages = 57–9 | year = 1985 | pmid = 3965972 | doi =10.1038/313057a0 | url = | author-separator = , | author2 = Liebisch DC | author3 = Gramsch C | display-authors = 3 | last4 = Herz | first4 = A | last5 = Weber | first5 = E | last6 = Evans | first6 = CJ | last7 = Esch | first7 = FS | last8 = Böhlen | first8 = P }}</ref><ref name="pmid4045460">{{cite journal | author = Liebisch DC, Seizinger BR, Michael G, Herz A | title = Novel opioid peptide amidorphin: characterization and distribution of amidorphin-like immunoreactivity in bovine, ovine, and porcine brain, pituitary, and adrenal medulla | journal = Journal of Neurochemistry | volume = 45 | issue = 5 | pages = 1495–503 | year = 1985 | month = November | pmid = 4045460 | doi = | url = }}</ref> In some brain areas, amidorphin is extensively further reduced into smaller fragments, such as the non-opioid peptide [[amidorphin-(8-26)]] which lacks the [[N-terminus|''N''-terminal]] [[Met-enkephalin|[Met]enkephalin]] [[peptide sequence|sequence]] of amidorphin; accordingly, [Met]enkephalin may also be a cleavage product of amidorphin.<ref name="pmid3456613">{{cite journal | author = Liebisch DC, Weber E, Kosicka B, Gramsch C, Herz A, Seizinger BR | title = Isolation and structure of a C-terminally amidated nonopioid peptide, amidorphin-(8-26), from bovine striatum: a major product of proenkephalin in brain but not in adrenal medulla | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 83 | issue = 6 | pages = 1936–40 | year = 1986 | month = March | pmid = 3456613 | pmc = 323199 | doi = 10.1073/pnas.83.6.1936| url = http://www.pnas.org/cgi/pmidlookup?view=long&pmid=3456613}}</ref>
'''Amidorphin''' is an [[endogenous]], [[C-terminus|C-terminally]] [[amide|amidated]], [[opioid]] [[peptide]] generated as a [[cleavage product]] of [[proenkephalin A]] in some mammalian species; in humans and most other species, the peptide is 1 residue longer and is not amidated. Amidorphin is widely distributed in the [[mammalian]] [[brain]], with particularly high concentrations found in the [[striatum]], and outside of the brain in [[adrenal medulla]] and [[posterior pituitary]].<ref name="pmid3965972">{{cite journal | author = Seizinger BR | title = Isolation and structure of a novel C-terminally amidated opioid peptide, amidorphin, from bovine adrenal medulla | journal = Nature | volume = 313 | issue = 5997 | pages = 57–9 | year = 1985 | pmid = 3965972 | doi =10.1038/313057a0 | author2 = Liebisch DC | author3 = Gramsch C | display-authors = 3 | last4 = Herz | first4 = A | last5 = Weber | first5 = E | last6 = Evans | first6 = CJ | last7 = Esch | first7 = FS | last8 = Böhlen | first8 = P | bibcode = 1985Natur.313...57S | s2cid = 4363051 }}</ref><ref name="pmid4045460">{{cite journal |vauthors=Liebisch DC, Seizinger BR, Michael G, Herz A | title = Novel opioid peptide amidorphin: characterization and distribution of amidorphin-like immunoreactivity in bovine, ovine, and porcine brain, pituitary, and adrenal medulla | journal = Journal of Neurochemistry | volume = 45 | issue = 5 | pages = 1495–503 |date=November 1985 | pmid = 4045460 | doi = 10.1111/j.1471-4159.1985.tb07218.x| s2cid = 12237293 }}</ref> The 26-residue peptide named amidorphin is found in several species including bovine (Bos taurus), sheep (Ovis aries), and pig (Sus scrofa). Humans and commonly studied lab animals (mice, rats) produce a 27-residue peptide that does not have an amidated C-terminal residue; this is due to the absence of a Gly in the precursor sequence and replacement with Ala, which is not a substrate for the amidating enzyme (Peptidyl-glycine alpha-amidating monooxygenase). The properties of the 27-residue peptide are presumably similar to those of amidorphin, although this has not been adequately tested.


In some brain areas, amidorphin is extensively further reduced into smaller fragments, such as the non-opioid peptide [[amidorphin-(8-26)]], or in humans, amidorphin-8-27. Cleavage of amidorphin into these smaller fragments releases the [[N-terminus|''N''-terminal]] [[Met-enkephalin|[Met]-enkephalin]] [[peptide sequence|sequence]] of amidorphin.<ref name="pmid3456613">{{cite journal |vauthors=Liebisch DC, Weber E, Kosicka B, Gramsch C, Herz A, Seizinger BR | title = Isolation and structure of a C-terminally amidated nonopioid peptide, amidorphin-(8-26), from bovine striatum: a major product of proenkephalin in brain but not in adrenal medulla | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 83 | issue = 6 | pages = 1936–40 |date=March 1986 | pmid = 3456613 | pmc = 323199 | doi = 10.1073/pnas.83.6.1936| bibcode = 1986PNAS...83.1936L | doi-access = free }}</ref>
== See also ==

==See also==
* [[Opioid peptide]]
* [[Opioid peptide]]


== References ==
==References==
{{Reflist}}
{{Reflist|2}}



{{Analgesics}}
{{Opioid peptides}}
{{Opioid peptides}}
{{Opioids}}
{{Opioidergics}}


[[Category:Analgesics]]
[[Category:Analgesics]]
[[Category:Neurotransmitters]]
[[Category:Neurotransmitters]]
[[Category:Opioids]]
[[Category:Opioid peptides]]

[[sr:Amidorfin]]