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Xylazine Tolazoline United States Department of Agriculture Agricultural Marketing Service | National Organic Program Document Cover Sheet https://www.ams.usda.gov/rules-regulations/organic/national-list/petitioned Document Type: ☐ National List Petition or Petition Update A petition is a request to amend the USDA National Organic Program’s National List of Allowed and Prohibited Substances (National List). Any person may submit a petition to have a substance evaluated by the National Organic Standards Board (7 CFR 205.607(a)). Guidelines for submitting a petition are available in the NOP Handbook as NOP 3011, National List Petition Guidelines. Petitions are posted for the public on the NOP website for Petitioned Substances. ☒ Technical Report A technical report is developed in response to a petition to amend the National List. Reports are also developed to assist in the review of substances that are already on the National List. Technical reports are completed by third-party contractors and are available to the public on the NOP website for Petitioned Substances. Contractor names and dates completed are available in the report. Xylazine/Tolazoline Livestock 1 2 Identification of Petitioned Substance 3 4 Chemical Names: 43 5 Xylazine 44 Trade Names: 6 Xylazine 45 Xylazine 7 Xylazine Hydrochloride 46 AnaSed® LA 8 Xylazine Monohydrochloride 47 Rompun® 9 N-(2,6-Diphenylmethyl)-5,6-dihydro-4H-1,3- 48 TranquiVed Injection 10 thiazin-2-amine 49 X-Ject SA 11 N-(2,6-Diphenylmethyl)-5,6-dihydro-4H-1,3- 50 XylaMed™Celactal 12 thiazin-2-amine hydrochloride 51 13 52 Tolazoline 14 Tolazoline 53 Tolazil™ 15 Tolazoline 54 Tolazoline® Injection 16 Tolazoline hydrochloride 55 Priscoline 17 2-Benzylimidazoline 56 Priscoline Hydrochloride 18 2-Benzyl-4,5-dihydro-1H-imidazole 57 Divascol 19 2-Benzyl-4,5-dihydro-1H-imidazole 58 Olitensol 20 hydrochloride 59 Lambril 21 60 Arterodyl 22 Other Names: 61 Priscol 23 Xylazine 62 24 Xylazine HCl 63 CAS Numbers: 25 Xylaxine 64 7361-61-7 (Xylazine) 26 Xylazin 65 23076-35-9 (Xylazine Hydrochloride) 27 Xilazina 66 59-98-3 (Tolazoline) 28 Xylazinium 67 59-97-2 (Tolazoline Hydrochloride) 29 Xylazine Chloride 68 30 69 Other Codes: 31 Tolazoline 70 EC No. 230-902-1 (Xylazine) 32 Tolazoline HCl 71 NSC No. 758142 (Xylazine) 33 Tolazoline Chloride 72 UNII No. 2KF9TP5V8 (Xylazine) 34 Imidaline Hydrochloride 73 EC No. 245-417-0 (Xylazine Hydrochloride) 35 Benzidazol 74 UNII No. NGC3S0882S (Xylazine Hydrochloride) 36 Benzalolin 75 EC No. 200-448-9 (Tolazoline) 37 Benzazoline Hydrochloride 76 NSC No. 35110 (Tolazoline) 38 Pridazole 77 UNII No. CHH9H12AQ3 (Tolazoline) 39 Phenylmethylimidazoline 78 EC No. 200-447-3 (Tolazoline Hydrochloride) 40 Tolazolinum 79 NSC No. 757353 (Tolazoline Hydrochloride) 41 Tolazolina 80 UNII No. E669Z6S1JG (Tolazoline Hydrochloride) 42 Peripherin 81 82 Summary of Petitioned Use 83 84 The United States Department of Agriculture (USDA)’s National Organic Program (NOP) has approved xylazine 85 and tolazoline for medicinal applications in organic livestock production. Both xylazine and tolazoline are 86 restricted to “use by or on the lawful written or oral order of a licensed veterinarian,” and must be followed by “a 87 meat withdrawal period of at least 8 days after administering to livestock intended for slaughter; and a milk 88 discard period of at least 4 days after administering to dairy animals,” at Title 7 of the Code of Federal 89 Regulations (CFR) Section 205.603. Tolazoline is further restricted for “use only to reverse the effects of sedation ___________________________________ January 4, 2019 Technical Evaluation Report Page 1 of 17 Compiled by Savan Group for the USDA National Organic Program Technical Evaluation Report Xylazine/Tolazoline Livestock 90 and analgesia caused by Xylazine,” at §205.603. This technical report outlines the veterinary applications of 91 xylazine for organic livestock production and serves to update a previous technical report from 2002 (USDA 92 2002b). 93 94 Characterization of Petitioned Substance 95 96 Composition of the Substance: 97 98 Xylazine 99 100 Xylazine (Figure 1) is a synthetic α2-adrenergic agonist, which Farbenfabriken Bayer developed in 1962 to 101 treat hypertension (Kreeger et al. 1986a, Kreeger et al. 1986b, Greene and Thurmon 1988, EMEA 1999, 102 Lester et al. 2012, Thies et al. 2017). Xylazine is a molecule in the clonidine family, and the basic sites on the 103 molecule (nitrogen and sulfur atoms with electron pairs) provide a basic structure important for the 104 biological absorption and distribution of the substance (Garcia-Villar et al. 1981, Greene and Thurmon 105 1988). Xylazine’s neurological activity has resulted in veterinary medicinal uses. The substance is 106 commonly administered as both the neutral compound (Figure 1) and its hydrochloride salt (PubChem 107 5707, PubChem 68554, Kreeger et al. 1986a, Kreeger et al. 1986b, Lester et al. 2012, Sigma-Aldrich 2014b, 108 Flecknell 2016, Sigma-Aldrich 2017). 109 110 Tolazoline 111 112 Tolazoline (Figure 1) is a synthetic α2-adrenergic antagonist, which also interacts with histamine and 113 cholinergic receptors (Goetzman and Milstein 1979, McIntosh and Waters 1979, Pawson 2008, Greenough et 114 al. 2012, Ebert 2013). Like xylazine, tolazoline is in the clonidine family and shares the basic attributes 115 (nitrogen atoms with electron pairs) that enable its rapid biological absorption and distribution 116 (Garcia-Villar et al. 1981, Greene and Thurmon 1988). Structural similarities with xylazine allow tolazoline 117 to compete with xylazine for biological binding sites. This provides the mode of action for its approved use 118 in organic livestock production as a reversal agent for xylazine (Levy et al. 1977, Goetzman and Milstein 119 1979, Kreeger et al. 1986a, Kreeger 1986b, Samanta et al. 1990, JECFA 1998a, JECFA 1998b, Pawson 2008). 120 Tolazoline’s neurological activity has resulted in its use in veterinary medicine and is commonly 121 administered as both the neutral compound (Figure 1) and its hydrochloride salt (PubChem 5504, 122 PubChem 6048, Kreeger et al. 1986a, Kreeger et al. 1986b, Sigma-Aldrich 2006, Pawson 2008, Rotta et al. 123 2011, Ebert 2013, Coleman and Cox 2014, Sigma-Aldrich 2014a). 124 H N N N HN S 125 Xylazine Tolazoline 126 127 Figure 1 128 129 Source or Origin of the Substance: 130 131 Xylazine 132 133 Xylazine is a synthetic substance produced by the multi-step reaction of 2,6-dimethylaniline, as shown in 134 Scheme 1 on the next page (Elliot and Ruehle 1985). January 4, 2019 Page 2 of 17 Technical Evaluation Report Xylazine/Tolazoline Livestock O O O O HN N O Nao S C S O S HN N OH C H N H2N OH S HCl HN N 135 136 137 Scheme 1 138 139 Tolazoline 140 141 Tolazoline is a synthetic substance that is produced by a one-pot process (i.e., no intermediates are isolated) 142 via the reaction of phenylacetaldehyde with ethylene diamine, with the incorporation of an iodine-based 143 oxidation process, as shown in Scheme 2 (Gogoi and Konwar 2006). 144 NH O 2 N H2N NH2 Base I2 / KI I N N HN HN 145 146 147 Scheme 2 148 149 Properties of the Substance: 150 The properties xylazine, xylazine hydrochloride, tolazoline, and tolazoline hydrochloride are summarized in 151 Table 1. 152 153 154 155 156 January 4, 2019 Page 3 of 17 Technical Evaluation Report Xylazine/Tolazoline Livestock 157 158 Table 1. Properties of xylazine, xylazine hydrochloride, tolazoline, and tolazoline hydrochloride Compound Xylazine Xylazine Tolazoline Tolazoline Hydrochloride Hydrochloride CAS No. 7361-61-7 23076-35-9 59-98-3 59-97-2 Molecular Weight 220.33 g/mol 256.79 g/mol 160.22 g/mol 196.68 g/mol Appearance White powder Solid White powder Solid Melting Point 141 oC N/A 66-69 oC 174-176 oC Solubility 0.5 g/L (methanol) N/A 373 mg/L (water) N/A 159 Sources: PubChem 5504, PubChem 5707, PubChem 6048, PubChem 68554, Sigma-Aldrich 2006, 160 Sigma-Aldrich 2014a, Sigma-Aldrich 2014b, Sigma-Aldrich 2017. 161 162 Specific Uses of the Substance: 163 164 Xylazine 165 166 The synthetic substance xylazine was originally developed to treat hypertension in humans (Kreeger et al. 167 1986a, Kreeger et al. 1986b, Greene and Thurmon 1988, EMEA 1999, Lester et al. 2012, Thies et al. 2017). 168 However, the prevalence of its side effects, including the onset of significant cardiac arrythmias, has 169 prohibited its use in human medicine (Green et al. 1981, EMEA 1999, Reyes et al. 2012). 170 171 Despite negative side effects in humans, xylazine is widely used in veterinary medicine, where the 172 frequency and danger of side effects are reduced. Xylazine, due to depression of the central nervous system 173 and cardiac outputs, is commonly used as a sedative and analgesic in veterinary medicine (EMEA 1999, 174 Lorenz et al. 2010, Lester et al. 2012, Otto and von Thaden 2012, Ruiz-Colon et al. 2014, Silva-Torres et al. 175 2014, Thies et al. 2017). Xylazine is the most common co-treatment for ketamine anesthetic applications 176 (Green et al. 1981, Kreeger et al. 1986a, Kreeger et al. 1986b, Saha et al. 2005, Reyes et al. 2012). 177 178 The United States Food and Drug Administration (FDA) has restricted the veterinary application of 179 xylazine with the designation “do not use in domestic food-producing animals,” at 21 CFR 522.2662. 180 Xylazine is also used as an emetic for cats, as an alternative to surgery to recover foreign objects (Thies et 181 al. 2017). 182 183 Tolazoline 184 185 Tolazoline is used in both human and veterinary medical applications. In human medicine, tolazoline is 186 used to treat hypotension, hypertension, newborn respiratory distress, and congenital heart disease 187 through interactions with α2-adrenergic and histamine receptors (Grover et al.
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