2,6-Dimethyl-L-tyrosine

Base Information

• Chemical Name: 2,6-Dimethyl-L-tyrosine
• CAS No.: 123715-02-6
• Molecular Formula: C11H15NO3
• Molecular Weight: 209.245
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID80154070
• Nikkaji Number: J500.692I
• Wikidata: Q27459305
• ChEMBL ID: CHEMBL180386
• Mol file: 123715-02-6.mol

Synonyms:2',6'-dimethyltyrosine;2,6-dimethyltyrosine

Chemical Property of 2,6-Dimethyl-L-tyrosine

Chemical Property:

• Melting Point: 239-240 °C (decomp)
• Boiling Point: 412.758 °C at 760 mmHg
• PKA: 2.34±0.20(Predicted)
• Flash Point: 203.429 °C
• PSA: 83.55000
• Density: 1.242 g/cm³
• LogP: 1.66370
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 209.10519334
• Heavy Atom Count: 15
• Complexity: 220

Purity/Quality:

99% ^*data from raw suppliers

L-2'',6''-Dimethyltyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1CC(C(=O)O)N)C)O
• Isomeric SMILES: CC1=CC(=CC(=C1C[C@@H](C(=O)O)N)C)O
• General Description: 2,6-Dimethyl-L-tyrosine (DMT) is an unnatural amino acid derivative that, when incorporated into opioid peptides like DMT-DPDPE, enhances potency at δ and μ opioid receptors while maintaining δ-selectivity. It significantly improves systemic analgesic activity, demonstrating increased efficacy in both in vitro and in vivo models, including crossing the blood-brain barrier to some extent. This modification highlights its utility in developing potent and selective δ-opioid receptor agonists for pain management.

Technology Process of 2,6-Dimethyl-L-tyrosine

There total 22 articles about 2,6-Dimethyl-L-tyrosine 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: 100.0%

C44H50N2O8 (1185756-58-4) → H-Dmt (123715-02-6)

Guidance literature:

With hydrogen iodide; for 3h; Reflux;

DOI:10.1016/j.tetasy.2009.06.004

Reference yield: 94.8%

C21H30N2O4S → H-Dmt (123715-02-6)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 3h;

Reference yield: 91.0%

O-ethoxy-2,6-dimethyl-L-tyrosine → H-Dmt (123715-02-6)

Guidance literature:

With hydrogen iodide; for 4h; Reagent/catalyst; Reflux;

upstream raw materials:

N-Acetyl-2,6-dimethyl-O-methyl-(S)-tyrosine methyl ester

1-iodo-2,6-dimethyl-4-methoxybenzene

Methyl-(Z)-α-acetamido-β-(2,6-dimethyl-4methoxyphenyl) acrylate

C₄₄H₅₀N₂O₈

Downstream raw materials:

2,6-dimethyl-N-<(phenylmethoxy)carbonyl>-L-tyrosine

2,6-dimethyl-(S)-tyrosine hydrochloride

D-arginyl-2,6-dimethyl-L-tyrosyl-L-lysyl-L-phenylalaninamide

α(S)-amino-N-<1(S)-<(1,1-dimethylethoxy)methyl>-2-(3-phenylpropoxy)ethyl>-4-hydroxy-2,6-dimethylbenzenepropanamide

Refernces

Systemic Analgesic Activity and δ-Opioid Selectivity in <2,6-Dimethyl-Tyr¹,D-Pen²,D-Pen⁵>enkephalin

10.1021/jm00082a008

The study investigates the synthesis and biological properties of the cyclic peptide [2,6-dimethyl-Tyr1,~Pen2,~Pen5]enkephalin (DMT-DPDPE, 2), which is a derivative of [~Pen~pPen~]enkephalin (DPDPE, 1). The researchers replaced the Tyrl residue of DPDPE with the unnatural amino acid 2,6-dimethyltyrosine (DMT) to create DMT-DPDPE. This modification significantly enhanced the peptide's potency at the δ opioid receptor (10-fold increase) and the μ receptor (35-fold increase), while maintaining substantial δ receptor selectivity. In in vitro tests, DMT-DPDPE was 86-fold more effective than DPDPE at inhibiting electrically stimulated contractions of the mouse vas deferens. In vivo, DMT-DPDPE demonstrated systemic analgesic activity, with an ED50 of 2.6 mg/kg in the writhing test and a 7-fold increase in potency over DPDPE in the intracerebroventricular hot plate test. Notably, DMT-DPDPE was effective in the hot plate test following subcutaneous administration, suggesting it can cross the blood-brain barrier to some extent. The study highlights the potential of DMT-DPDPE as a potent and selective δ opioid receptor agonist with systemic analgesic properties.

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