Chemistry:Azaprocin

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Short description: Opioid analgesic drug
Azaprocin
Azaprocin 1.svg
Clinical data
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC18H24N2O
Molar mass284.403 g·mol−1
3D model (JSmol)
Melting point170 to 175 °C (338 to 347 °F)
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Azaprocin is a drug which is an opioid analgesic with approximately ten times the potency of morphine, and a fast onset and short duration of action.[1][2][3] It was discovered in 1963, but has never been marketed.

The derivative substituted on the phenyl ring with a p-nitro group is more potent than the parent compound, around 25× the potency of morphine.[4] The ring-opened 2,6-dimethylpiperazine analogues are also active,[5] and a large family of opioid analgesic compounds derived from this parent structure have been developed over the last 40 years.[6][7][8][9][10][11][12][13][14][15] One analogue, AP-237, has been used in China to treat the pain caused by cancer.[citation needed]

References

  1. ↑ "Bicyclic Homologs of Piperazine. VI.1Synthesis and Analgesic Activity of 3-Substituted 8-Propionyl-3,8-diazabicyclo[3.2.1]octanes". Journal of Medicinal Chemistry 6 (6): 764–6. November 1963. doi:10.1021/jm00342a030. PMID 14184943. 
  2. ↑ "Bicyclic Homologs of Piperazine. VII.1Synthesis and Analgesic Activity of 3-Aralkenyl-8-propionyl-3,8-diazabicyclo[3.2.1]octanes". Journal of Medicinal Chemistry 8 (3): 326–31. May 1965. doi:10.1021/jm00327a010. PMID 14323140. 
  3. ↑ "[Effect of analgesic drugs on the conditioned behavior of rats]". Bollettino Chimico Farmaceutico 107 (2): 120–6. February 1968. PMID 5730115. 
  4. ↑ "Interaction of 3,8-diazabicyclo (3.2.1) octanes with mu and delta opioid receptors". Pharmacological Research Communications 20 (5): 383–94. May 1988. doi:10.1016/s0031-6989(88)80014-6. PMID 2843931. 
  5. ↑ "2,6-Dialkylpiperazines. IV. 1-Propionyl-4-substituted cis-2,6-dimethylpiperazines structurally related to the analgetic 8-acyl-3,8-diazabicyclo[3.2.1]octanes". Journal of Medicinal Chemistry 11 (3): 592–4. May 1968. doi:10.1021/jm00309a039. PMID 5656502. 
  6. ↑ "Interaction of 3,8-diazabicyclo (3.2.1) octanes with mu and delta opioid receptors". Pharmacological Research Communications 20 (5): 383–94. May 1988. doi:10.1016/s0031-6989(88)80014-6. PMID 2843931. 
  7. ↑ "Computer-aided structure-affinity relationships in a set of piperazine and 3,8-diazabicyclo[3.2.1]octane derivatives binding to the mu-opioid receptor". Journal of Computer-Aided Molecular Design 7 (5): 557–71. October 1993. doi:10.1007/bf00124362. PMID 8294946. Bibcode: 1993JCAMD...7..557B. 
  8. ↑ "Antinociceptive action of DBO 17 and DBO 11 in mice: two 3,8 diazabicyclo (3.2.1.) octane derivates with selective mu opioid receptor affinity". Naunyn-Schmiedeberg's Archives of Pharmacology 356 (5): 596–602. November 1997. doi:10.1007/pl00005095. PMID 9402039. 
  9. ↑ "Synthesis and mu-opioid receptor affinity of a new series of nitro substituted 3,8-diazabicyclo[3.2.1]octane derivatives". Farmaco 53 (8–9): 557–62. 1998. doi:10.1016/s0014-827x(98)00065-2. PMID 10081818. 
  10. ↑ "Benzocondensed derivatives as rigid analogues of the mu-opioid agonist 3(8)-cinnamyl-8(3)-propionyl-3,8-diazabicyclo[3.2.1]octanes: synthesis, modeling, and affinity". Farmaco 53 (10–11): 667–74. 1998. doi:10.1016/s0014-827x(98)00084-6. PMID 10205853. 
  11. ↑ "Synthesis, molecular modeling, and opioid receptor affinity of 9, 10-diazatricyclo[4.2.1.1(2,5)]decanes and 2,7-diazatricyclo[4.4.0. 0(3,8)]decanes structurally related to 3,8-diazabicyclo[3.2. 1]octanes". Journal of Medicinal Chemistry 43 (11): 2115–23. June 2000. doi:10.1021/jm991140q. PMID 10841790. 
  12. ↑ "Synthesis, modelling, and mu-opioid receptor affinity of N-3(9)-arylpropenyl-N-9(3)-propionyl-3,9-diazabicycl". Farmaco 55 (8): 553–62. August 2000. doi:10.1016/s0014-827x(00)00036-7. PMID 11132733. 
  13. ↑ "N-3(9)-arylpropenyl-N-9(3)-propionyl-3,9-diazabicyclo[3.3.1]nonanes as mu-opioid receptor agonists. Effects on mu-affinity of arylalkenyl chain modifications". Bioorganic & Medicinal Chemistry 10 (6): 1929–37. June 2002. doi:10.1016/s0968-0896(01)00436-9. PMID 11937351. 
  14. ↑ "Synthesis of novel diazatricyclodecanes (DTDs). Effects of structural variation at the C3' allyl end and at the phenyl ring of the cinnamyl chain on mu-receptor affinity and opioid antinociception". Bioorganic & Medicinal Chemistry 11 (18): 4015–26. September 2003. doi:10.1016/s0968-0896(03)00373-0. PMID 12927864. 
  15. ↑ "Synthesis of 3,6-diazabicyclo[3.1.1]heptanes as novel ligands for the opioid receptors". Bioorganic & Medicinal Chemistry 14 (3): 676–91. February 2006. doi:10.1016/j.bmc.2005.09.045. PMID 16243530. 



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