Ameya Purohit: Created page with "{| class="infobox" style="float:right; clear:right; width:22em; margin:0 0 1em 1em; padding:0.2em; border:1px solid #a2a9b1; background:#f8f9fa; color:#202122; font-size:88%; line-height:1.5em; border-spacing:3px" |+ style="font-size:125%; font-weight:bold; padding:0.2em" | Drug |- | colspan="2" style="text-align:center" | |- ! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | Watchedfields | changed |- ! scope="row" style="text-align:left; v..."

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|+ style="font-size:125%; font-weight:bold; padding:0.2em" | Drug
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! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | Excretion
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|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | Cas number ref
| ??
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | Cas number
| 19036-73-8
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | PubChem CID
| 15897
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | Iuphar ligand
| 215
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | Chemspiderid ref
| chemspider
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | ChemSpider
| 15108
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | Unii ref
| FDA
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | UNII
| CLX07A6ZIY
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | ChEBI
| 125411
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | ChEMBL
| 1979333
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | Synonyms
| 3-Trifluoromethylamphetamine; 3-TFMA; Desethylfenfluramine; JP-92


|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | Iupac name
| 1-[3-(trifluoromethyl)phenyl]propan-2-amine
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | C
| 10
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | H
| 12
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | F
| 3
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | N
| 1
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | SMILES
| FC(F)(F)c1cccc(c1)CC(N)C
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | InChI
| 1S/C10H12F3N/c1-7(14)5-8-3-2-4-9(6-8)10(11,12)13/h2-4,6-7H,5,14H2,1H3
|-
! scope="row" style="text-align:left; vertical-align:top; padding-right:0.6em" | InChI key
| MLBHFBKZUPLWBD-UHFFFAOYSA-N
|}

'''नॉरफेनफ्लुरामाइन''' (Norfenfluramine), या '''3-ट्राइफ्लुओरोमेथिलएम्फेटामाइन''' (3-trifluoromethylamphetamine), [[एम्फेटामाइन]] (amphetamine) परिवार की एक कभी बाजार में न उतारी गई [[दवा]] (drug) है और यह [[भूख कम करने वाली दवा|भूख कम करने वाली दवाओं]] (appetite suppressants) [[फेनफ्लुरामाइन]] (fenfluramine) और [[बेनफ्लूरेक्स]] (benfluorex) का एक प्रमुख [[सक्रिय मेटाबोलाइट]] (active metabolite) है। यह [[रासायनिक यौगिक]] (chemical compound) दो [[एनैन्टीओमर्स]] (enantiomers) का एक [[रेसेमिक मिश्रण]] (racemic mixture) है, जिनकी गतिविधियाँ अलग-अलग होती हैं, जिन्हें [[डेक्सनॉरफेनफ्लुरामाइन]] (dexnorfenfluramine) और [[लेवोनॉरफेनफ्लुरामाइन]] (levonorfenfluramine) कहा जाता है।<ref name="RothmanClarkPartilla2003">(June 2003). "(+)-Fenfluramine and its major metabolite, (+)-norfenfluramine, are potent substrates for norepinephrine transporters". ''The Journal of Pharmacology and Experimental Therapeutics''. 305 (3) 1191–1199. doi:[https://doi.org/10.1124/jpet.103.049684 10.1124/jpet.103.049684].</ref><ref name="SetolaHufeisenGrande-Allen2003">(June 2003). "3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro". ''Molecular Pharmacology''. 63 (6) 1223–1229. doi:[https://doi.org/10.1124/mol.63.6.1223 10.1124/mol.63.6.1223].</ref>

== औषध विज्ञान (Pharmacology) ==
नॉरफेनफ्लुरामाइन एक [[सेरोटोनिन-नॉरपेनेफ्रिन रिलीजिंग एजेंट]] (SNRA) के रूप में कार्य करता है<ref name="RothmanBaumann2006" /><ref name="RothmanClarkPartilla2003" /> और यह एक [[शक्तिशाली]] (potent) सेरोटोनिन [[5-HT2A रिसेप्टर|5-HT2A]], [[5-HT2B रिसेप्टर|5-HT2B]], और [[5-HT2C रिसेप्टर|5-HT2C रिसेप्टर]] [[एगोनिस्ट]] (agonist) है।<ref name="RothmanBaumannSavage2000" /> नॉरफेनफ्लुरामाइन के दोनों [[एनैन्टीओमर्स]] [[मोनोअमाइन रिलीजिंग एजेंट]] (monoamine releasing agents) के रूप में सक्रिय हैं, हालाँकि [[डेक्सनॉरफेनफ्लुरामाइन]] [[लेवोनॉरफेनफ्लुरामाइन]] की तुलना में अधिक शक्तिशाली है।<ref name="RothmanClarkPartilla2003" /> इसी तरह, दोनों एनैन्टीओमर्स सेरोटोनिन [[5-HT2 रिसेप्टर|5-HT2 रिसेप्टर]] एगोनिस्ट के रूप में सक्रिय हैं, लेकिन डेक्सनॉरफेनफ्लुरामाइन लेवोनॉरफेनफ्लुरामाइन की तुलना में अधिक शक्तिशाली है।<ref name="RothmanBaumannSavage2000">(December 2000). "Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications". ''Circulation''. 102 (23) 2836–2841. doi:[https://doi.org/10.1161/01.cir.102.23.2836 10.1161/01.cir.102.23.2836].</ref>

नॉरफेनफ्लुरामाइन सेरोटोनिन रिलीज करने वाले के रूप में फेनफ्लुरामाइन के समान शक्तिशाली है, लेकिन नॉरपेनेफ्रिन और [[डोपामाइन]] रिलीज करने वाले के रूप में काफी अधिक शक्तिशाली है।<ref name="RothmanBaumann2006" /><ref name="RothmanClarkPartilla2003" /> यह दवा सेरोटोनिन 5-HT2 रिसेप्टर्स के एगोनिस्ट के रूप में भी फेनफ्लुरामाइन से कहीं अधिक शक्तिशाली है।<ref name="RothmanBaumannSavage2000" />

[[हृदय वाल्वों]] (heart valves) पर सेरोटोनिन 5-HT2B रिसेप्टर्स पर नॉरफेनफ्लुरामाइन की क्रिया [[ट्राइकसपिड वाल्व]] (tricuspid valve) पर [[हृदय]] के [[फाइब्रोब्लास्ट्स]] (fibroblasts) के [[कोशिका प्रसार]] (cell proliferation) के बाद [[हृदय विफलता]] (heart failure) के एक विशिष्ट पैटर्न की ओर ले जाती है, जिसे [[कार्डियक फाइब्रोसिस]] (cardiac fibrosis) के रूप में जाना जाता है।<ref>(July 2005). "Molecular determinants for the interaction of the valvulopathic anorexigen norfenfluramine with the 5-HT2B receptor". ''Molecular Pharmacology''. 68 (1) 20–33. doi:[https://doi.org/10.1124/mol.104.009266 10.1124/mol.104.009266].</ref> इस [[दुष्प्रभाव]] (side effect) के कारण दुनिया भर में [[एनोरेक्टिक]] (anorectic) दवा के रूप में [[फेनफ्लुरामाइन]] को वापस ले लिया गया और [[यूरोप]] में [[बेनफ्लूरेक्स]] को वापस ले लिया गया।<ref>(2009-12-18). [http://www.emea.europa.eu/pdfs/human/referral/benfluorex/Benfluorex_81503309en.pdf European Medicines Agency recommends withdrawal of benfluorex from the market in European Union]. European Medicines Agency.</ref>

सेरोटोनिन 5-HT2A रिसेप्टर एगोनिस्ट के रूप में कार्य करने के बावजूद, नॉरफेनफ्लुरामाइन को गैर-[[मतिभ्रमकारी]] (non-hallucinogenic) बताया गया है।<ref name="GumpperRoth2024">(January 2024). "Psychedelics: preclinical insights provide directions for future research". ''Neuropsychopharmacology''. 49 (1) 119–127. doi:[https://doi.org/10.1038/s41386-023-01567-7 10.1038/s41386-023-01567-7].</ref> हालाँकि, फेनफ्लुरामाइन की बड़ी खुराक के साथ कभी-कभी मतिभ्रम की सूचना मिली है, जो स्वयं नॉरफेनफ्लुरामाइन की तुलना में बहुत कमजोर सेरोटोनिन 5-HT2A रिसेप्टर एगोनिस्ट है, लेकिन यह एक प्रमुख सक्रिय मेटाबोलाइट के रूप में नॉरफेनफ्लुरामाइन का उत्पादन करता है।<ref name="GumpperRoth2024" /> डेक्सनॉरफेनफ्लुरामाइन कृंतकों में [[हेड-ट्विच रिस्पॉन्स]] (head-twitch response) उत्पन्न करता है, जो [[साइकेडेलिक दवा]] (psychedelic drug) के प्रभावों का एक व्यवहारिक प्रॉक्सी है।<ref name="VickersEastonMalcolm2001">(2001). "Modulation of 5-HT(2A) receptor-mediated head-twitch behaviour in the rat by 5-HT(2C) receptor agonists". ''Pharmacol Biochem Behav''. 69 (3–4) 643–652. doi:[https://doi.org/10.1016/s0091-3057(01)00552-4 10.1016/s0091-3057(01)00552-4].</ref>

नॉरफेनफ्लुरामाइन को [[ट्रेस अमाइन-एसोसिएटेड रिसेप्टर 1]] (TAAR1) के एगोनिस्ट के रूप में कार्य करते हुए पाया गया है।<ref name="pmid22037049">(December 2011). "Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class". ''Bioorganic & Medicinal Chemistry''. 19 (23) 7044–7048. doi:[https://doi.org/10.1016/j.bmc.2011.10.007 10.1016/j.bmc.2011.10.007].</ref> डेक्सनॉरफेनफ्लुरामाइन एक बहुत ही कमजोर मानव TAAR1 एगोनिस्ट है (10,000 nM की सांद्रता पर स्क्रीन में अधिकतम का 43%), जबकि लेवोनॉरफेनफ्लुरामाइन एक मानव TAAR1 एगोनिस्ट के रूप में निष्क्रिय है।<ref name="pmid22037049" />

{| class="wikitable" style="font-size:small;"
|+ [[Monoamine releasing agent|Monoamine release]] of norfenfluramine and related agents (Half maximal effective concentration, nM)
|-
! Compound !! data-sort-type="number" | Norepinephrine !! data-sort-type="number" | Dopamine !! data-sort-type="number" | Serotonin !! Ref
|-
| [[Dextroamphetamine]] || 6.6–7.2 || 5.8–24.8 || 698–1,765 || <ref name="RothmanBaumannDersch2001">(January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". ''Synapse''. 39 (1) 32–41. doi:[https://doi.org/10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3 10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3].</ref><ref name="BaumannPartillaLehner2013">(2013). "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". ''Neuropsychopharmacology''. 38 (4) 552–562. doi:[https://doi.org/10.1038/npp.2012.204 10.1038/npp.2012.204].</ref><ref name="Blough2008" /><ref name="GlennonDukat2017">(2017). "Neuropharmacology of New Psychoactive Substances (NPS)". 32 19–47. Springer. ISBN 978-3-319-52442-9. doi:[https://doi.org/10.1007/7854_2016_41 10.1007/7854_2016_41].</ref>
|-
| [[Levoamphetamine]] || 9.5 || 27.7 || No data || <ref name="Forsyth2012">(22 May 2012). [https://scholarworks.uno.edu/td/1436/ Synthesis and Biological Evaluation of Rigid Analogues of Methamphetamines]. ''ScholarWorks@UNO''.</ref><ref name="Blough2008">(July 2008). [https://books.google.com/books?id=QCagLAAACAAJ Dopamine Transporters: Chemistry, Biology and Pharmacology]. 305–320. Wiley. ISBN 978-0-470-11790-3.</ref><ref name="Liu2018">Liu, Yi. (28 March 2018). [https://dsc.duq.edu/etd/829/ Structural Determinants for Inhibitor Recognition by the Dopamine Transporter]. ''Duquesne Scholarship Collection''.</ref><ref name="BloughPagePartilla2005">(2005). "Structure–activity relationship studies of DAT, SERT, and NET releasers".</ref>
|-
| [[Dextromethamphetamine]] || 12.3–14.3 || 8.5–40.4 || 736–1,292 || <ref name="RothmanBaumannDersch2001" /><ref name="BaumannAyestasPartilla2012">(2012). "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". ''Neuropsychopharmacology''. 37 (5) 1192–1203. doi:[https://doi.org/10.1038/npp.2011.304 10.1038/npp.2011.304].</ref><ref name="Blough2008" /><ref name="PartillaDerschBaumann1999" />
|-
| [[Levomethamphetamine]] || 28.5 || 416 || 4,640 || <ref name="RothmanBaumannDersch2001" /><ref name="Blough2008" />
|-
| [[Ethylamphetamine|Dextroethylamphetamine]] || 28.8 || 44.1 || 333.0 || <ref name="FitzgeraldGannonWalther2024">(March 2024). "Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones". ''Neuropharmacology''. 245. doi:[https://doi.org/10.1016/j.neuropharm.2023.109827 10.1016/j.neuropharm.2023.109827].</ref><ref name="Nicole2022">Nicole, Lauren. (2022). [https://www.proquest.com/openview/a207e98868b4a9c5ac9296fb24abbcd8/ In vivo Structure-Activity Relationships of Substituted Amphetamines and Substituted Cathinones]. ''ProQuest''.</ref>
|-
| [[Fenfluramine]] || 739 || >10,000 (Reuptake inhibitor) || 79.3–108 || <ref name="RothmanBaumann2006" /><ref name="RothmanBaumann2009" /><ref name="RothmanBaumannDersch2001" /><ref name="RothmanClarkPartilla2003"/>
|-
|   [[Dexfenfluramine]] || 302 || >10,000 || 51.7 || <ref name="RothmanBaumann2006" /><ref name="RothmanBaumann2009" /><ref name="RothmanBaumannDersch2001" /><ref name="RothmanClarkPartilla2003" />
|-
|   [[Levfenfluramine]] || >10,000 || >10,000 || 147 || <ref name="RothmanBaumann2006" /><ref name="RothmanBaumann2009" /><ref name="RothmanClarkPartilla2003" /><ref name="RothmanBaumann2002a">(July 2002). "Therapeutic and adverse actions of serotonin transporter substrates". ''Pharmacology & Therapeutics''. 95 (1) 73–88. doi:[https://doi.org/10.1016/s0163-7258(02)00234-6 10.1016/s0163-7258(02)00234-6].</ref>
|-
| Norfenfluramine || 168–170 || 1,900–1,925 || 104 || <ref name="RothmanBaumann2006" /><ref name="RothmanBaumann2009" /><ref name="RothmanClarkPartilla2003" /><ref name="SetolaHufeisenGrande-Allen2003" />
|-
|   [[Dexnorfenfluramine]] || 72.7 || 924 || 59.3 || <ref name="RothmanBaumann2006" /><ref name="RothmanBaumann2009" /><ref name="RothmanClarkPartilla2003" />
|-
|   [[Levnorfenfluramine]] || 474 || >10,000 || 287 || <ref name="RothmanBaumann2006" /><ref name="RothmanBaumann2009" /><ref name="RothmanClarkPartilla2003" />
|-
| [[Phentermine]] || 28.8–39.4 || 262 || 2,575–3,511 || <ref name="RothmanBaumannDersch2001" /><ref name="Blough2008" /><ref name="PartillaDerschBaumann1999">(1999). [https://archives.nida.nih.gov/sites/default/files/180.pdf#page=261 Problems of Drug Dependence 1999: Proceedings of the 61st Annual Scientific Meeting, The College on Problems of Drug Dependence, Inc]. 180 1–476 (252).</ref>
|-
| [[Chlorphentermine]] || >10,000 (reuptake inhibitor) || 935–2,650 || 18.2–30.9 || <ref name="RothmanBaumannDersch2001" /><ref name="PartillaDerschBaumann1999" />
|-
| colspan="5" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Notes:''' The smaller the value, the more strongly the drug releases the neurotransmitter. The [[bioassay|assay]]s were done in rat brain [[synaptosome]]s and human [[potency (pharmacology)|potencies]] may be different. See also [[Monoamine releasing agent#Activity profiles|Monoamine releasing agent § Activity profiles]] for a larger table with more compounds. '''Refs:''' <ref name="RothmanBaumann2003">(October 2003). "Monoamine transporters and psychostimulant drugs". ''Eur J Pharmacol''. 479 (1–3) 23–40. doi:[https://doi.org/10.1016/j.ejphar.2003.08.054 10.1016/j.ejphar.2003.08.054].</ref><ref name="RothmanBaumann2006">(2006). [https://zenodo.org/record/1235860 Therapeutic potential of monoamine transporter substrates]. ''Current Topics in Medicinal Chemistry''. 6 (17) 1845–1859. doi:[https://doi.org/10.2174/156802606778249766 10.2174/156802606778249766].</ref><ref name="RothmanBaumann2009">(May 2009). "Serotonergic drugs and valvular heart disease". ''Expert Opin Drug Saf''. 8 (3) 317–329. doi:[https://doi.org/10.1517/14740330902931524 10.1517/14740330902931524].</ref>
|}

{| class="wikitable" style="font-size:small;"
|+ Norfenfluramine and related agents at the [[serotonin]] [[5-HT2 receptor|5-HT2 receptor]]s
|-
! rowspan="2" | Compound !! colspan="3" | [[5-HT2A receptor|5-HT2A]] !! colspan="3" | [[5-HT2B receptor|5-HT2B]] !! colspan="3" | [[5-HT2C receptor|5-HT2C]]
|-
! [[Affinity (pharmacology)|Ki]] (nM) !! Half-maximal effective concentration (nM) !! Maximal efficacy (%) !! [[Affinity (pharmacology)|Ki]] (nM) !! Half-maximal effective concentration (nM) !! Maximal efficacy (%) !! [[Affinity (pharmacology)|Ki]] (nM) !! Half-maximal effective concentration (nM) !! Maximal efficacy (%)
|-
| [[Fenfluramine]] || 5,216 || 4,131 || 15% || 4,134 || No data || No data || 3,183 || No data || No data
|-
|   [[Dexfenfluramine]] || 11,107 || >10,000 || No data || 5,099 || 379 || 38% || 6,245 || 362 || 80%
|-
|   [[Levofenfluramine]] || 5,463 || 5,279 || 43% || 5,713 || 1,248 || 47% || 3,415 || 360 || 84%
|-
| Norfenfluramine || 2,316 || No data || No data || 52.1 || No data || No data || 557 || No data || No data
|-
|   [[Dexnorfenfluramine]] || 1,516 || 630 || 88% || 11.2 || 18.4 || 73% || 324 || 13 || 100%
|-
|   [[Levonorfenfluramine]] || 3,841 || 1,565 || 93% || 47.8 || 357 || 71% || 814 || 18 || 80%
|-
| [[Phentermine]] || >10,000 || Inactive or No data || Inactive or No data || >10,000 || Inactive or No data || Inactive or No data || >10,000 || 1,394 || 66%
|-
| [[Chlorphentermine]] || No data || >10,000 || No data || No data || 5,370 || No data || No data || 6,456 || No data
|-
| colspan="10" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Notes:''' (1) The smaller the Ki or EC50 value, the more avidly the drug binds to or activates the receptor. The higher the Emax value, the more effectively the drug activates the receptor. (2) All values are for human receptors except for the 5-HT2A and 5-HT2C Ki values, which are for the rat receptors. '''Refs:''' <ref name="RothmanBaumannSavage2000" /><ref name="RothmanBaumann2009" /><ref name="RothmanBaumann2006" />
|}

== See also ==
* [[Substituted amphetamine]]

== References ==
<div class="reflist" style="column-width:30em; font-size:90%">
<references />
</div>

[[Category:3-(Trifluoromethyl)phenyl compounds]]
[[Category:5-HT2A agonists]]
[[Category:5-HT2B agonists]]
[[Category:5-HT2C agonists]]
[[Category:Anorectics]]
[[Category:Cardiotoxins]]
[[Category:Human drug metabolites]]
[[Category:Monoaminergic neurotoxins]]
[[Category:Psychedelic phenethylamines]]
[[Category:Serotonin receptor agonists]]
[[Category:Serotonin-norepinephrine releasing agents]]
[[Category:Substituted amphetamines]]
[[Category:TAAR1 agonists]]

----
''स्रोत:'' अंग्रेज़ी विकिपीडिया के "Norfenfluramine" लेख पर आधारित।
''मूल लेख:'' https://en.wikipedia.org/wiki/Norfenfluramine
''यह लेख स्वचालित रूप से तैयार किया गया है।''

नॉरफेनफ्लुरामाइन - Revision history

Ameya Purohit at 15:26, 10 October 2026

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