Chlornaltrexamine: Difference between revisions

| verifiedrevid = 409723733

|ImageFile=Chlornaltrexamine.svg

|ImageSize=200px

|IUPACName= 6-(Bis(2-chloroethyl)amino)- 17-(cyclopropylmethyl)- 4,5-epoxy- (5-α,6-β)- morphinan- 3,14-diol

|OtherNames=α-chlornaltrexamine

| CASNo=67025-94-9

| PubChem=5486190

| SMILES=O[C@@]13[C@]2([C@@H]5[C@H](N(CCCl)CCCl)CC3)C4=C(C=CC(O)=C4O5)C[C@H]1N(CC6CC6)CC2

| Formula=C₂₄H₃₂Cl₂N₂O₃

| MolarMass=467.43 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

| MainHazards=

| FlashPt=

| Autoignition=

'''Chlornaltrexamine''' is an irreversible mixed agonist-antagonist for [[mu opioid receptor|μ-]][[opioid]] [[Receptor (biochemistry)|receptors]], which forms a [[covalent bond]] to the [[active site]]. It is 22 times more potent than morphine. Its alkylating group is a bis(chloroalkyl)amino-residue similar to that of the [[nitrogen mustard]]s.<ref>{{cite journal |doi=10.1021/jm00205a002 |author=Portoghese PS, Larson DL, Jiang JB, Takemori AE, Caruso TP |title=6β-[N,N-Bis(2-chloroethyl)amino]-17-(cyclopropylmethyl)-4,5α-epoxy-3,14-dihydroxymorphinan(chlornaltrexamine) a potent opioid receptor alkylating agent with ultralong narcotic antagonist actitivty |journal=J. Med. Chem. |volume=21 |issue=7 |pages=598–9 |year=1978 |month=July |pmid=209185 }}</ref>

<ref>{{cite journal |doi=10.1021/jm00188a008 |author=Portoghese PS, Larson DL, Jiang JB, Caruso TP, Takemori AE |title=Synthesis and pharmacologic characterization of an alkylating analogue (chlornaltrexamine) of naltrexone with ultralong-lasting narcotic antagonist properties |journal=J. Med. Chem. |volume=22 |issue=2 |pages=168–73 |year=1979 |month=February |pmid=218009 }}</ref>

<ref>{{cite journal |doi=10.1126/science.86208 |author=Caruso TP, Takemori AE, Larson DL, Portoghese PS |title=Chloroxymorphamine, and opioid receptor site-directed alkylating agent having narcotic agonist activity |journal=Science |volume=204 |issue=4390 |pages=316–8 |year=1979 |month=April |pmid=86208 |url=http://www.sciencemag.org/cgi/pmidlookup?view=long&pmid=86208}}</ref>

<ref>{{cite journal |author=Caruso TP, Larson DL, Portoghese PS, Takemori AE |title=Pharmacological studies with an alkylating narcotic agonist, chloroxymorphamine, and antagonist, chlornaltrexamine |journal=J. Pharmacol. Exp. Ther. |volume=213 |issue=3 |pages=539–44 |year=1980 |month=June |pmid=6162947 |url=http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=6162947}}</ref>

<ref>{{cite journal |doi=10.1016/0024-3205(80)90485-3 |author=Caruso TP, Larson DL, Portoghese PS, Takemori AE |title=Isolation of selective 3H-chlornaltrexamine-bound complexes, possible opioid receptor components in brains of mice |journal=Life Sci. |volume=27 |issue=22 |pages=2063–9 |year=1980 |month=December |pmid=6259471 }}</ref><ref>{{cite journal | journal =J. Med. Chem. | year = 1983 | volume = 26 | title =Alkylation of opioid receptor subtypes by α-chlornaltrexamine produces concurrent irreversible agonistic and irreversible antagonistic activities. | pmid =6300401 | issue = 4 | pages = 503 | doi = 10.1021/jm00358a009 | author = Sayre LM, Takemori AE, Portoghese PS}}</ref>

{{reflist}}

[[Category:Morphinans]]