Dpdpe

Base Information

• Chemical Name: Dpdpe
• CAS No.: 88373-73-3
• Molecular Formula: C30H39 N5 O7 S2
• Molecular Weight: 645.801
• DSSTox Substance ID: DTXSID201008102
• Nikkaji Number: J261.772B
• Wikipedia: DPDPE
• Wikidata: Q27077106
• Metabolomics Workbench ID: 66387
• ChEMBL ID: CHEMBL31421

Synonyms:Bis Pen Enkephalin;Bis Penicillamine Enkephalin;Bis-Pen-Enkephalin;Bis-Penicillamine-Enkephalin;D Pen2, D Pen5 Enkephalin;D Pen2, L Pen5 Enkephalin;D-Pen2, D-Pen5-Enkephalin;D-Pen2, L-Pen5-Enkephalin;D-Pen5-Enkephalin D-Pen2;D-Penicillamine (2,5)-Enkephalin;DPDPE;DPDPE(SH)2;DPLPE;Enkephalin, D-Penicillamine (2,5)-;Enkephalin, Pen(2,5)-;Enkephalin, Penicillamine (2,5)-;L-Pen5-Enkephalin D-Pen2

Chemical Property of Dpdpe

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1038.6°C at 760 mmHg
• Flash Point: 581.9°C
• PSA: 250.55000
• Density: 1.38g/cm³
• LogP: 3.18970
• Storage Temp.: −20°C
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 645.22909095
• Heavy Atom Count: 44
• Complexity: 1040

Purity/Quality:

99%, ^*data from raw suppliers

Enkephalin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C(C(=O)NCC(=O)NC(C(=O)NC(C(SS1)(C)C)C(=O)O)CC2=CC=CC=C2)NC(=O)C(CC3=CC=C(C=C3)O)N)C
• Isomeric SMILES: CC1([C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(SS1)(C)C)C(=O)O)CC2=CC=CC=C2)NC(=O)[C@H](CC3=CC=C(C=C3)O)N)C
• Biological functions: The effects of morphine represent the functions of endogenous opioid peptides via DOR, KOR, and MOR. In the central nervous system, morphine causes analgesia, euphoria, sedation, miosis (constriction of the pupils), truncal rigidity, nausea, and vomiting, and decreases the rate of respiration and the cough reflex. In the gastrointestinal system, morphine causes constipation, constriction of the biliary smooth muscle, and esophageal reflux, and reduces gastric motility, digestion in the small intestine, and peristaltic waves in the colon. In other smooth muscles, morphine causes urinary retention, depresses renal function, and decreases uterine tone. In the skin, morphine causes itching, sweating, and flushing of the face, neck, and thorax. In the cardiovascular system, morphine decreases blood pressure and the heart rate if the cardiovascular system is stressed. In the immune system, morphine decreases the cytotoxic activity of natural killer cells and the formation of rosettes by human lymphocytes. Morphine also induces behavioral restlessness. Pharmacological studies using both delta agonists and delta antagonists in rodents show that the anxiolytic activity of the opioid tone is mediated by DOR. Although Met-ENK was originally identified as a neuromodulator that interacts with DOR, this peptide was subsequently revealed to be a tonically active regulator of cell proliferation as well.
• Uses: [D-Pen2,5]-Enkephalin hydrate (DPDPE) has been used to study the pharmacodynamic and pharmacokinetic capabilities of polyethylene glycol (PEG) conjugate of DPDPE in rodents. It has been used to study the tendency of opiate self-administration in male Long-Evans rats, in ventral tegmental area (VTA).
• Clinical Use: Nalmefene reduces alcohol consumption in adults with alcohol dependence. Morphine and hydromorphone are used in the treatment and management of severe pain. Naltrexone is used alongside behavioral therapy both for opiate addiction and for alcohol dependency. Naloxone is used to reverse narcotic depression.

Technology Process of Dpdpe

There total 3 articles about Dpdpe which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

D-pen2,5-enkephalin (100111-01-1) → (4S,7S,13S)-13-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-7-benzyl-3,3,14,14-tetramethyl-6,9,12-trioxo-1,2-dithia-5,8,11-triaza-cyclotetradecane-4-carboxylic acid (88373-73-3,88373-72-2,88381-29-7)

Guidance literature:

With tetrachloromethane; tetrabutyl ammonium fluoride; water; In tetrahydrofuran; dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1016/S0040-4039(99)00926-0

Reference yield:

BOC-glycine (4530-20-5) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + Boc-Tyr-OH (3978-80-1) + Nα-Boc-(S-p-MeBzl)-D-penicillamine (115962-34-0) → (4S,7S,13S)-13-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-7-benzyl-3,3,14,14-tetramethyl-6,9,12-trioxo-1,2-dithia-5,8,11-triaza-cyclotetradecane-4-carboxylic acid (88373-73-3,88373-72-2,88381-29-7)

Guidance literature:

Multistep reaction;

DOI:10.1021/ja954241w

Reference yield:

BOC-glycine (4530-20-5) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + Boc-Tyr-OH (3978-80-1) + Nα-(tert-butyloxycarbonyl)-S-(p-methylbenzyl)-D-penicillamine → (4S,7S,13S)-13-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-7-benzyl-3,3,14,14-tetramethyl-6,9,12-trioxo-1,2-dithia-5,8,11-triaza-cyclotetradecane-4-carboxylic acid (88373-73-3,88373-72-2,88381-29-7)

Guidance literature:

Multistep reaction;

DOI:10.1021/jm00110a010

upstream raw materials:

BOC-glycine

N-tert-butoxycarbonyl-L-phenylalanine

Boc-Tyr-OH

N^α-Boc-(S-p-MeBzl)-D-penicillamine

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