Nitric Acid → Citrulline Dinitrate

HRID 1046715Notes

Reaction equation

HRID 1046715 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].[NH2:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH2:13])=[O:12].[N+:17]([O-:20])([OH:19])=[O:18].[NH2:21][C@H:22]([C:30]([OH:32])=[O:31])[CH2:23][CH2:24][CH2:25][NH:26][C:27]([NH2:29])=[O:28]>O>[N+:1]([O-:4])([OH:3])=[O:2].[N+:17]([O-:20])([OH:19])=[O:18].[NH2:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH2:13])=[O:12].[N+:1]([O-:4])([OH:3])=[O:2].[N+:1]([O-:4])([OH:3])=[O:2].[N+:1]([O-:4])([OH:3])=[O:2].[NH2:21][C@H:22]([C:30]([OH:32])=[O:31])[CH2:23][CH2:24][CH2:25][NH:26][C:27]([NH2:29])=[O:28]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 9750CitrullineHCID 86628843Citrulline Nitrate

Product 2

HCID 86628841Citrulline DinitrateHCID 86628842Citrulline Trinitrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Applicants have cost-effectively synthesized Citrulline Nitrate by combining nitric acid and Citrulline, mixing with water, and leaving to crystallize. Further nitratization can take place, yielding Citrulline Dinitrate or Citrulline Trinitrate. An alternative implementation may comprise using Nitrous Acid (HNO2) instead of Nitric Acid (HNO3), thus yielding Citrulline Nitrite. Citrulline Nitrite has the same effects as Citrulline Nitrate, the only difference being that it requires one less step to yield Nitric Oxide (NO—). Mixed salts may also be used, such as in the non-limiting example of Citrulline Nitrate-Orotate.

Workup

  1. customleaving
  2. customto crystallize

Sources & evidence

ORD record
ord-ccefffc0915e48e9b0e6cce0a54cf6af
Source dataset
uspto-grants-2013_10
Patent number
US08569369B2

Reaction notes

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